OT
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`ATOMS
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`INT ODUCT
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`11
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`

`
`.tO.12
`
`Bureau ot Standards Journal
`
`1lsearch
`
`dOlfltLOliS 01
`
`when
`iroin
`to
`the ifldiVldUiL 510111 CILdflifl
`lL aonne roufiguranon is
`by its mirror flange Vant
`replaced
`Hod illustaterl
`this nde quite plainly
`its application to the carho
`However at hat time the
`hydrate field as will be discussed below
`pcrimenl al data were lacking to establish its
`alid ty in the sugar
`io9 the deeolopmeni of experimental carloh dra.to
`ronp
`hi
`die in-try wa sufficient or Hudson
`io apply the superposition rub
`by us method of CoItsldefiiig only the rotations of
`the first nsyni
`mc iii
`carbon and the rest of
`the molecule and to determine the
`the first carbon atom and the rotation of he re3t
`aptical rotation of
`lie compared all kinds of derivatives by his method
`of the molecule
`tnd by this way of compar1on showed that
`the principle of optical
`to make comoarisoll
`UpL.IpOSIC ion bORIS app oximn telv
`in ordci
`bet eeen substences whose structure differs considerably he ixiade
`rules isoiotation or approximations
`The corrcla
`number of
`ho
`of rot ation in lie sugar group by hini and others showed
`hat
`exist many devielionsi
`from his rides which intricate Ihat
`the
`the various aym
`given group on the rotatory power of
`influence of
`toms is manifested
`iie carbon
`the sugar molecule
`throughout
`was alilicipa led
`the theoiy of optical superpo itioti
`test of
`cant Hoff4 in 1t94 who .taees
`that when there are evera
`cuibon
`at oins then
`be added
`ot- subtracted
`rnotric
`action
`the lout- pciiose tvpcs OH CHOI-I3 we should have
`to
`lhus for
`die following rotation
`
`tact
`
`Yo.i
`
`No.3
`
`No.4
`
`jual ABC
`
`No
`and No
`ilne the 5110 01 No
`khe oiation of aralinosc probably tile higbst shoula he equal
`to
`rthese nod the cia eted fourth type taken
`dir
`tahions of vyloac
`ether
`idet airy be pu in the farm of four simultaneous eqim
`tofi
`jit
`thi cc voriahks and
`ions w-lnoll
`contain oi ily
`the experimental
`ron any three of
`xaiue if
`..
`and
`Ii
`detci-muied
`the equal ions
`heck
`ho burl ci equanori
`apahed in lie given eas
`his
`lieo-y
`II one had
`imiPr series of coinpount1 ih rh
`fLute
`rn-ovcd
`wouLd bo strong eindenc that all
`the compounds in he
`ehcckcci
`.rc cii sioihir
`r1S11 ealnoitio
`lie experimental
`oh
`ti
`roa.suning has not been posibe beeauae of he lack of
`of Liii
`rxlein and sulb-irn expermen tel data The prbiem is far more
`thu vent
`cmhl cat innate at
`early dale
`rnijth-c.i
`hat
`Li .r cr in the litbt
`of modern kiiovlecigc
`the ring .trUctP1C
`tIpIi
`i_ tr it should now he possible to rear-li
`the
`the desired goid
`data wc avoilublo
`cM
`ho p-
`
`ii
`
`.1
`
`Tb
`
`Pop
`
`.1 ru VI
`
`polT
`Vt
`1.O ICr .flCStIli
`
`it.p
`
`Lo4rcIur
`
`ru rn .1 c.
`
`...i
`
`1PR2014-01126- Ex 1023
`
`

`
`ptirai
`
`Iotewn cad iio aflOlVre
`
`Supii so
`
`Ii43
`
`for
`
`hi
`
`Ii
`
`Ii
`uuihor is attcrnjttng to piepare those eolnpokmd ncceaaty
`the calculation am sic eJn of
`ov
`rotator
`of all
`the optical
`the
`different asymmetric carbon etomr in the bco
`.oars and nwihv
`II
`IP
`Ci
`en
`cat
`tiP in
`and
`.tii
`ioie of c.dirIilosc
`ifs if at
`1110 optisa
`ii
`at
`been leLerinIneO iiec aloe so mpk-te
`3methy1 dgulosides hwt
`the conipu Lotion of he aptied tota 1on of cncli
`the data ne-essurv lot
`.hc several asynina vie eni bun othms in the hexoso .ntgan and in
`of
`The values obtained for the iotvorv pm of
`the methyl glycosides
`ie of particoro
`the different asymmetric c.nbon
`stoma
`in1eeSt
`rotadon
`the
`glvtosidee ma be
`the normal aldolsexoc sugar end iwtiut
`of all
`The numerical values for the at preriit mincm norinel
`calculated
`form of 1idose dtaoe daliotc and da1tr
`sc ano the- cot-respond
`An ottenpi
`is hein made to
`ing methyl gyco-adca arc predicttoi
`the i1ttiiai
`one at
`trnr
`inea.au
`rotation
`ii a--e
`fl501i 1.0
`racy be found tn tb
`he optical
`rotnLcwo whoit
`.-l4dose
`lutuic
`If
`cheek
`values IL will be .tiong evidncc
`the predicted
`the
`diii
`sugars involved in the calculations ha inuIar rn structures
`BY TIlE AGREEMENT
`DETERMINATION
`OF RING STRUCTURE
`OR DEViATION FROM TE-TE TNEOI.Y OE OPrICAL SUPER
`VTtTP
`POtrTION
`
`hccaue they are the PY alues flail
`
`rile
`
`ticat
`
`111.1
`
`lit
`
`11
`
`the
`
`Ii
`
`pea
`Ide
`
`sir
`ci
`
`ci
`
`Ic
`
`ita--ted
`
`rinr
`
`iii
`
`ti
`
`the
`
`iii
`
`ot
`
`i1oi.t
`
`the jtI
`
`it
`
`as
`
`tt
`
`ci
`
`--
`
`ii
`
`of
`c-il ml
`
`-di
`
`ia hcn cant
`.rj3 prcaenfsd i.hc 1he.iy
`the
`f-Toil
`sifi.iO1i
`ri
`ansi.ic-i
`the red iewf sugiis
`to
`hues
`ianbojucniii
`Inis heefl
`fe uvt dis
`it
`OIU
`eli
`n-in
`ia 11
`-numetnc cvbor
`Toflens
`heel st
`the rc inctirii
`the educipa sgar bitt disorcrv ri
`tritu SC lu
`hr. OLL of
`in
`iS
`The opth ii
`moderii eoncpL
`si ructre of the sugnl
`lit
`roru tioji
`torn wa t-terinuc-i
`hen
`lhOti b-
`the aeuoakielr.dc
`cc
`of
`of brilliant ree cles h.rs di-veltpci
`Jiudrer who b- C1i
`of oprh 01 siipe position into the mc
`fel
`the theor
`oil at 11w
`Un
`1511 of
`hsh 141lOfl n-
`the 11 IIO dP. 1.101 ugns
`the .c
`the cta sugars tid tue rolt
`the or eleeule
`the adforin
`the so La lit
`antI the rotation
`fl of
`-a
`Ill
`in
`fl-
`the diierenre bet eon the molecular rctaums of
`that
`iJe
`cb.ta first
`si-cars and hi-ir derivatie- 2a is
`/3 hoLIS of
`ci On
`ill Tile olidehvde
`nearh constant quari ii tv and secourfly that
`forns of
`the
`01.1
`in witic mjy the first carbon is
`hose derii ati
`IUI- aldow siaat
`es of
`affected hi molecular jO Latjoiw whose 411.111
`1sii1ma1elv cs.juoii
`to LIce suns 26 of
`the inulcuI
`fat ma of
`cml
`the
`otations of
`are found to the
`tic sugar Certain in.eeptiour
`rides pa
`any in tile mnnse i-barn nose
`ad lxeic ei
`if
`it ili
`led to
`t_ ii
`021 13
`Pr .15
`2-In aJ3
`aL
`10tvec
`iLtatory lower ijd S0atj.c
`rtflr
`102
`
`ii
`
`5r -un
`
`mm ii 0-Sd
`
`pr
`
`50
`
`1PR2014-01126- Ex 1023
`
`

`
`buceeii of Stooda Jr ioucnat uf Resea c/i
`
`that among hi 1nown derivative
`TiO L3pI
`of
`1nd
`iaIuioac
`.mis tIere occur sthsthncc
`of priou rilig types which ac
`ouni to the observod osceptienal
`rotations end that
`conipcirntive
`tances belonging to the ank ring type slow normal eoinpuiii lie
`so
`The Itvpothesis
`ottiojia which accounts fat
`ialuts
`the nornial
`id uPbeat
`arious nihtances
`-cries which
`ion of
`to the d.ilfernt
`tile
`They
`uav goro Lisly attacked ly Tiiii orth and ITirst
`he iostuia ed
`and /3mannosc as being not necessariiy dissimilar in img
`rcirurd
`the dtvrgence in ork ci rotation may ho
`ore and beievo the
`aucd by tie spcial ansngemaritof hvdIo\v
`iannose
`groups jr
`coal tl
`cola ted sugars rhamnose arid lyxost
`IVXISO ivllose rotation 70 also exceptional
`their studies they
`IOIUId
`flew
`
`Tn
`
`rot
`
`unit
`
`ddt lonal sup
`hypot hsis has recently received
`tEcvt-vt-r
`ii udsiiri
`oct in tim preparation by Daic 12 of
`caiciuiir ehloide double corn
`new form of ad--manncse whose jotation agrees with the
`ooiind of
`I-i rdrn foi
`ha
`1uhi ted
`of /drmrnriosi-
`in ui
`cl-ri
`fllR ii
`Icosidee
`the sugars ant
`corn pa rison of the optical rotations ot
`given series cf eomlioPilciS have or have not
`imlitntes that
`-incr Form Tim cilig sti-ucture
`to be
`said ser
`iSsUneCl
`c-c cuuiuiou
`same as
`Ii
`the rag stniLure of any iubstancr-
`in the sndcs whose
`-crur tore i_s ctabiishe-l by othiec nu-iliods Tin ring structures
`by
`1cc-v substances
`die results obtained
`are dnrii cii
`of
`thu-sc-
`uncthvhn.wn
`studici
`
`OF THE GLYCOSIDES
`OF RING STRUC1UL
`DE lERMINATION
`PROM METHYLATION STUDIES
`
`co
`
`l-ir
`
`showed that
`in lfOS Pirdie and Ti-vine
`rhe hvciroxvl
`groups iii
`.thyl ghcoside roiild he replaced by nethrc-zi1
`reaps by recalls of
`vi ldide and cult oc ohdc
`Since a11 Pie hi dccxvi giounS in the
`alucese aic ihoched the iiin struhurc is as
`icatiharl penlaaic-ftvl
`The normal
`and ct pentarnthvi gin
`mm-ti
`to
`rsomeicc
`fiaeci
`when hydrol sed Lv roads are coot cited nte tetramcthc
`Boti
`the terramethvl glucose exhiL-t nutarotattan
`of
`an.1 give the sniec
`and
`pon er whroh shows thee
`lunal rotatort
`thi giucore hree the carrie ring st.uctur-e
`ten
`hecen tl Wcrlfi-oiu
`Lowe
`have siroan iiat
`be uairs
`tctlaiIetIul
`giucoc
`ldfj
`rorind Lv dilul
`alkalies dii ceth
`to tetramcihcT macinose which
`Lis flait
`glucose have simi
`tetrrmathI mennose and tetrainethyl
`idcnce on the locai non of
`iii-cct
`the ring
`thY
`cincr st u-act
`roe
`Iv ox ha loll of
`tin inethi
`la.ted sugars to the COrrC-
`ticlds Charlion .hirwortheml Pent
`found that
`no icctone pu-op--i rid from 11.1- normal forms et slii.ose gahuc tose
`noumo.arhriurc and
`lose bt
`into Lyle ti
`fl4 the aldose- coil
`ilL bi
`to O\id
`-ii
`iou
`in
`tjo-i
`ied li
`hiSsi
`carrre1 uriluccte tb-it
`lactone
`e.c lonuecl
`
`st sugar
`
`nt.1 .urncd
`
`Lrv
`
`iiIl
`
`Iii
`
`Ii u-st
`
`Thu
`uapicl
`ibis cOflClUIOfl
`
`Ji -i
`
`.1
`
`.1
`
`110
`
`__
`
`llJLl
`
`ill-i
`
`JI
`
`i_ Ar li
`si Lj.li...I..5r.1Ij2llSI551il1li
`.ii
`.S.1-.Si
`dllli
`
`n.ilp21s511i21
`
`125
`
`1PR2014-01126- Ex 1023
`
`

`
`UpUeoi d.ja ici Tha.j
`
`.St1ocer
`
`143
`
`10 So G11
`ia ben confir.ried
`of th various moth In ted
`the detrrodation
`b%
`acd
`5uga acids by mt
`the epecred pcoouco
`zidaton
`tcrameth
`from the norma
`erratnethi 0f0flIC acid
`prepd ed
`uoe on it cu atid
`dcWon
`70 p.r vent
`Iotrt
`ieid ol
`hch in h.n to thai
`me iIiO\yg1U nile avid
`rityIa ted rnar
`rh
`ring struoure
`has
`the third neth
`The fooiiiitioa of
`tire dhtilic bta so
`nod other cindar coïnpounci
`-forin of Pisdter
`indicates
`ea11e.l
`rugar solrticn an cquiiibriam nioc vh1 between
`that mn
`rnicnoer
`ring- fonns
`.A pointed out
`hc1p anci PLrve the
`of differeni
`iated suit ii which might be prepvroi
`from
`ring sti
`iteture of
`Tiet
`suh soluijon would not dotermine the tiler stracture of he origixial
`uJtnhtha roahon atom
`Ji0fl subsntiitjon
`suent
`on the
`tue o.vgen ming is nor stqbls
`end 1ud.aL1y it
`as in the glacosides
`dae not
`uoa fru cr mthv
`be
`ion
`flenno
`ra
`in
`oh tuned froni
`tie of al vcodcs
`he cornet
`aslc.Iried that
`ring struct
`triothiatnin triios but
`no nng stuel
`that
`ires of
`the svgars arc
`ihi
`hv nictbvaton
`iL G-nicthvl
`au WU iv neI hI Itioii sr1pa tiitt
`iino liv
`iethvi galnctosid
`arni
`
`Iit
`
`iaeli
`
`itt
`
`ii
`
`.-
`5n
`ir
`tL
`wncsc rtha.Ions were ustd cuìt wich be
`not hero
`alien SIUQWs
`to ltnoea
`010
`i-rng atiijrh-tp
`arid moth
`rep01 od
`uiosides it
`in bra ant
`I1
`11
`it
`the other crvstaIitheirivcoedc
`01 th 5iCr
`crc alenand be
`urn of
`rlPg trictureI
`gar ui
`to in
`Iire ccur
`th.t
`in dct
`Cj.i
`cmpu ad
`The rotal cii of each suir
`isautndoii
`the corrcpondhig
`rotation of
`glveoside Fee Wears of
`
`11
`
`t1
`
`ii
`
`it
`
`tt
`
`31cr-cal
`
`it
`
`Ii
`
`cf
`
`cf
`
`by l.ulrthv
`il1rts nov.y
`has
`ion
`II
`
`Ic
`
`it
`
`II
`
`tire
`
`ith the
`fheocing
`
`Tie
`
`TjfiflZ
`
`fl
`
`irh ish.L
`
`sig0rB3SöiJ0
`
`If
`
`La
`and
`IWCiifli ter
`suiInei
`the valuet oi
`fl9rfç
`on substances have smu1er ring tricIirns
`Thee only encep
`rho
`hudson
`or ii
`and
`tions as pieviousiv found by
`he
`nhimanose
`00
`umen ii Va UC elmows
`hal
`tea
`of
`the
`conIparleoti
`3w oj
`uP1 odii mD
`is usumed
`31 iO 11 Ojil arueth% cLinuririosde
`
`Itt
`-- Oj and hence
`
`li
`.U Pr
`
`.Cileb
`
`23
`
`iTO
`
`Prs
`
`sn
`
`51
`
`2411
`
`Lvrrth tSr sn Iiiil
`.0
`
`ir
`
`.1
`
`ti
`
`.o ri
`
`TnT
`
`iy .rijin-rii
`Ori
`
`Iur..
`
`SC
`iii
`g.iO
`
`.3
`
`u.n Sx
`
`rart ti-at
`
`Ti
`
`ii
`
`in SiC
`ci.n S.c
`Slit in
`1352 1951 P5
`
`i.ion
`..o
`ri
`ILLL SOLi
`1525
`nThJn
`plsn.iid Tn aathvat
`o.o ipuiiyi uisIi1
`luijun
`iuilShed TI thi
`hue b.iusc il
`
`unIT
`
`CrC iOflhik.tli
`
`ainl
`
`Itrnnse .nr prch3S Tin irucrurr
`he s. i_linT before
`th mtL Ci in tudi-
`
`ill
`
`1PR2014-01126- Ex 1023
`
`

`
`t046
`
`Bi-eas
`
`ta IaiiLs Jou.rrnd cJ Research
`
`so
`
`it
`
`is
`
`thl.\ bd ng to ih sonic seOiOs
`.440 from
`The vslue of
`hot
`l-rumnu.c
`ohio from the methyl glvco
`does not check
`the
`10 .IntIi
`it hie
`different
`ide
`indicates
`that
`ring structure
`The value of
`therefore excluded from he ealculations
`ii 2.000 from 8dJ.vxose 70 does not check
`the value of
`8760 iroiii amethyl dFxosde and so it
`is also excluded from
`the cokulaions
`The values of
`as weli as the data USed in
`arid
`re given in Table
`he calculations
`
`-4--
`
`caLL Optical
`
`lOtion of
`
`the aldose sajnrs and qlgcosidcs
`
`.-21
`
`r-n
`
`-siisnr
`
`03-Il
`
`i-IEslgilId
`
`-cg1ucowI
`
`vii1ursLI.2
`
`t-0.333 0003
`
`14
`
`ii
`
`4-113
`
`--
`
`-IL.--
`
`-r-20.34211S40i
`4-L20
`11.337i.._
`
`ii 3OI
`
`--32.5
`-33
`
`----4.300
`
`--- 4333
`
`I_F12r
`
`3033
`
`-17
`
`---u7
`
`4.7
`144
`
`34-it333
`---337330
`
`4-.6433
`-35J1
`
`-415.rifl
`12530._1.iI0
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`4-ii14
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`415a714-37.340
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`15.550
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`if
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`
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`
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`14-
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`175
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`
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`
`141O
`710
`
`27.o
`
`17
`
`LI
`
`1-
`
`71
`
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`
`51
`L-
`
`LI
`
`0- I73Prr_o 533
`HolrOIiI 4.m L.m.Tp1 1q17
`faii -05 37 1073 59
`73
`-tmerCis SwII
`2785
`1524
`ft--fl31t-I 0.- srsv thins 3.-p
`223
`.1a.o w-c n.ec 110_n hc aull ro c-rft wh0h will 53 suiooqIcntlv pulIihc.l Tin rotian
`he eth
`cr 33-d frn
`h1or31c doohic onuoun-f
`of a- d-rolss
`tL 1Cit3f7 5oPl
`fm_n
`..h5
`oSol
`The iota- 10
`100311-
`tallizvl
`_n If 4rn1 lOy 113 13 52
`33111cr L31 330r
`l1L
`39
`1055
`101 34
`-.14
`.771
`lyf.33 Sc-c
`
`-II
`
`-1
`
`4-
`
`0-
`
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`
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`
`10-n 1-
`-c do
`5i01
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`
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`
`12 304
`
`1.33334
`
`c..1-hm_
`
`ft
`
`51- -no
`
`Ar_nt
`
`703
`
`l2I
`
`IL CALCULATION OF THE NUMERICAL VALUE FOR THE
`OPTICAL ROTARY POWER OF THE VARIOUS ASYMME
`TRIC CARBON ATOMS
`
`METHOD OF CALCULATION
`
`.c vs.Ln-
`
`tlio
`
`li
`
`0mg sti w-t.1re for the sugars the are repre
`the
`lit
`105
`c-c diffor
`the stereorner1 orrangeinent
`of
`the
`-mis
`-..c
`c3i-hcn ato only one form is givers
`The methyl
`n--.kL-h-.ht
`
`iI
`
`Sill
`
`--
`
`1PR2014-01126- Ex 1023
`
`

`
`i.n
`
`Vpttcut Rotation ood Rina
`
`trtena gar Groai
`
`t47
`
`difler
`
`from thc
`
`first etl IS roplo ONI by metlIo\y group
`
`Sugiiri- only in tha
`
`he vdro on tb4
`
`IT
`
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`
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`
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`
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`
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`
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`
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`
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`
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`
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`
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`
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`01.1
`
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`
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`
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`
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`I____________
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`
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`
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`
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`
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`
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`
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`
`TI
`
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`rn ri
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`
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`
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`
`J._____
`
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`
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`
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`
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`
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`
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`
`LI
`
`05_C
`
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`
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`
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`
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`
`ii
`
`Ft
`
`LI
`
`OH
`
`.I____.___.______
`
`n-
`
`2on-Tidering
`
`IILtICILI
`
`0.1
`
`first
`
`cm
`
`the rot
`
`of
`
`Ifl
`
`the ror
`of
`Ui
`jtoit
`Lion
`tile
`tiIi
`in the g1ycossdv IlnI
`the ji 1101 earooxi
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`1115 SIJiiF
`B4
`It ThiN of
`the io1eeuI..r
`rot
`The rO id icr0
`111011 oI1ow
`tlvcosnIe are gi-e by eiun t1OiL
`and
`the lWCSLri0S n-ce deiolLIIn ted with
`the variouE cisbon
`of
`OSI1S
`II 1XItO5PSN ls toe3
`ond
`letter
`the capital
`IUI dCS.CiUit0d
`tlie rGIa for
`the Vflr1Oo CUI0JL
`letter
`with the small
`tonis
`to hsrinuih thrn
`in the glcoides
`rirLed wIth nil
`rer-ent
`are
`The trm in the lOUOtiOflS
`from th vaies derired iriin the utnr-
`are conjdered to be poiiive when the bydroxyl group in the oiwor
`lies aheve as 505511 iii Foiinuln
`1101 bel.on cifld n-cu.tsve nijon tr
`to VI ncluie
`
`t50a15
`2I.xrr-it
`.t_giuoa017P._/_1_TtR..i_2I30ii
`t2 8c_ii.tcocaic-.JfftTIhRi
`-4-3120
`40
`Hrc
`71-LUtLfltIO
`mannoc aHIlL-.H-Ii--l 1700
`-xd-gn1utosc Cp If
`ft
`-ihe
`25000
`$dgothefos
`ft --- ft4-4-h
`L.O13
`t4-fR5
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`
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`79 3nathvi dgiucnsidni a---I- If1 jI-- lPoOe
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`-tn- R- -- Tf --RIR- -4373U
`1fl arncthl
`18-iiwIh1 d-galactosida 4Rft1----It--
`30
`ftl-42l1i4rft
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`_L_99 000
`igui-u ido
`iguioTidc- -ai..I 2i--R3R-iIf--
`114 amethyl
`10.140
`ngars qm ci
`
`Tb 70511 on 04 7IL Iis 044100
`Tb glyo1.hi ci
`701C 5001
`see 11 nee
`rbn at-
`Ii
`en c1cuLl
`thL ser-LO
`JIudso 10 1905
`Iii
`fir
`TI
`ed
`io 41 ill
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`lo 11 OCt75 107 Stud 111 -iOOtflO 10
`4.01 CLI aU07
`Ito TplmriC lif5t
`05 ors rot ikrabis oJ lh
`tl
`Us 21
`-15140
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`due to IT
`OiiretOiotjtot of 5-15 TrIletUrcI TI Cot-lOon
`04 th imrlb 7700 710111 nh- puose gIycoirtCs
`goon
`1150 resored to ic the some cr0 is
`U..iOfl -57 W75
`
`tonI
`
`II
`
`II
`
`to-
`
`1PR2014-01126- Ex 1023
`
`

`
`101-S
`
`Buraa
`
`Standards Journa oj ResearJl
`
`Vol.4
`
`ri -- awl
`
`IS 4-
`
`17
`18 -d-Ly.üi-c-
`
`-- Pr-I- 0--I-
`-I- ti -r2-
`r- -r3F
`
`-I 13800
`r4 120.250
`
`-1-825
`
`PLNT05E
`
`aUGAIh
`
`rrNTOSE GLYCOImE0
`19 aisiethI 1x looide
`i-E-rs-l
`20 3nethvI dxdoside
`-r1ir
`1arid 11110101 a.j c2 r3
`2l cinetii
`raimnohle --Qr2- r1
`22 3moth2
`231 c-methyl cilyxosidc a-r2 -5ir4 9740
`Ie CfJUz2t1OIs
`p1st geii mnv he coived for
`flliit1Onc
`the optieal
`carbon
`of
`the differeBt asynitneti-ic
`or subtracting
`iu t1cidir
`he equanons in such manner as to elmimstc all
`the variables except
`The computations are given below-
`one
`
`125210
`10740
`-1 2840
`-f 40200
`
`OF THE VARIOUS
`ROTATIONS
`1ALCULATION OF OPTICAL
`ASYMMETRIC cARBON ATOMS
`
`IIEXOSE STalES
`
`24 .c- giactme..d_gahiet.ice
`ai1.ucie ficgIlicoiw
`ilpal doshk
`20 vsrih
`r1ciIactmide ---j5--rerivI
`27 ami
`hvt ei-glucosde9merhy1 4-gFaosidc.
`28 umci
`lii dgUlO$ide6nwth
`d-guloside
`vimarnwe
`20 aJgiuaooc
`30 amethyl glucohide--asieth.il dmninoide
`31 a-1-gdsec-d-gaiaetose.
`32 unelh ilguloside a--awl Lyl Jgulaei oidc
`ti ui side
`gnhct
`nethI
`31 asiucosna dga1actoc
`35 2d.-giuenoed i-aiaetose
`tg1leOs1d umel hvl
`.30 aTielhVl
`37 8mti1iyi dsripeodc
`.18 adgiihe I-ailfliO.LIOO6C 2awj
`30
`iguloide-I-asnetnyl dinaiinoidc
`1-methyl
`
`ilga1actosde
`dgalaetosidc
`
`1EYTOS EIti F-
`
`ili
`icie8iiiethsl
`2-0 ixICftii\l
`amehvi
`41 mil hvl
`lambi
`-12 wl1C10--- udlyxos
`13 amethyl -xyIo$idea-methyl 1-lvxs
`
`lnidc
`lurabinosol_
`
`44 81ar 2a
`
`15
`
`a-methyl l-arahro-icIi-amethy1 dhywcld6
`46 vcwl
`3iaraljnosc
`47 asw h-I ixslocidc
`firiel hvl
`imnhli dxdosideamethvl
`18
`
`larahnn.itl-.
`1a raid nosidi-
`
`10 34O2a11
`880 2a
`37 4002a
`3PO3O2e
`36 0%J-2a
`11 900- 2R
`15 30021
`14 80U2R-
`--- 16 780 21
`Ii 0211
`6002i
`-.5 9202Th
`7502R4
`220 -21t4
`
`__.
`
`-- 35 9S0--2a
`--1-37 -420 2-
`12 07522
`15 5002r2
`-10 3702r
`12 S$09r
`
`12 450
`15 020--
`13 5802
`
`ii
`
`Tic
`
`con cf
`
`f.r
`
`-i
`
`is
`
`cc4ei
`
`lie
`
`ii
`
`It
`
`Phrui- ri viii
`lSTIC of is for
`-d-ulasi plus d-ninncaiJhan
`4sdn.rmina Ly eqtioon cu and cr Th.-jc cl .1i
`is oi ion-I
`ly sUltrcthi
`ons of ad -Wriso ai 1r iinc
`ounih r01
`ii frr
`11 so ci d.-s Icons-
`vi d-juise
`is.o-
`i-ian-- nc
`nine DLIi
`I- di Cr cm ion if 2o
`US of ir 0114101 au Hot
`Pet 054 sir hi
`al--
`is-
`idon hoc s.n ii
`rh-nn ao-n 4t iriiVt Uci4
`no for acia 1.7i wt
`na apI ppc-.s
`lie ro_iüi
`Eu fat
`souU for rie henor
`pt nIT ry ti- nnrncr cn
`el
`1en inc C.UiiCfl 1cr 20
`
`1PR2014-01126- Ex 1023
`
`

`
`Opt fcal
`
`iotou
`
`th trLitrz .a
`
`Grovp
`
`1049
`
`StThIIIARY OF RESULTS
`
`Pente eres
`
`lyS 350
`R7 400
`
`450
`
`t75
`
`Olf
`R-
`
`1L4
`
`520
`650
`-S 2113
`.40
`00
`
`rJf- --3 PI 3Th
`
`.-
`
`4-7Th
`200
`-7 150
`
`cc Ootrit
`
`1O1
`
`IlL DISCUSSION OF RESULTS
`
`tim of
`th rco
`cmporson
`0ori
`tony 0r
`ti th
`th I-coside sls tha in
`md that
`
`of
`he
`
`iluga
`
`-ye
`
`ho cir IL.If
`
`the liriponcal
`
`-a1uev
`
`toe af
`
`tile
`
`ti-ia atSUflit101
`
`thor
`
`the
`
`tho v.rbs as- nmletri
`IO.0 flS 0111
`rot TH If
`To1 ShoWS
`IVP
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`nath
`
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`
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`
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`
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`fist hl-e itl
`ihe I-i
`Iho
`01
`tho same order
`ceies ore of
`the 10-1
`se ie ho
`atoms in the haoMf
`tha rot tioa ci
`5N
`a-icc
`110111
`10
`01 1-ro ci ps
`Cr100
`tart
`iiic
`-10 dora
`ha haa.c
`l1l
`01th011 if
`si-
`
`01
`
`ITh
`
`th- T..V
`
`the hrrt ctin
`or
`
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`
`ifil
`
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`
`-5 scrI._s
`
`-IiiOl
`
`f-
`
`1%
`
`Iiu
`
`th.-rhc rota t.cn
`
`ho didcri Ocr -i
`
`fir
`
`rjoesidc
`thc
`
`-1
`
`15
`
`i1ih0OtOTt Oil
`rhe
`i.P1-
`tuc torts ILStfIII
`rIot he SOS
`ato-ri. ws
`
`Ii
`
`oil
`
`10
`
`ii- ins
`
`iS irI11P1C cirt.ion
`
`ad-alit-c
`
`mtnpl-rc c-ai
`ion
`he Dc-v all
`the ta tmv powei
`jf
`
`IS aoi
`OtojIl
`dare -er iiatoi-rii
`ht
`111010
`is vci-v uno
`
`is clot
`I-a
`futh.r
`dc on
`J-lroorth rI-
`sit
`fi
`at
`t-iLafl -cc he lot
`ore those on to her
`it
`it /iflIC-
`inn th .t.iO Catr1cir
`end
`tstcrv poe of rio hi arm am
`for lie
`it can not ho orphined or
`
`iLi-
`
`Ll1 Ic 1v
`-_i1 v-a
`
`..he
`
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`
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`
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`
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`
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`
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`
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`
`.010-
`
`COMPP.kISON
`
`THE i.IETY GLYCO-
`OF THE P.cTST1ONs
`WITH lEE ROTATIONS OF THE SUGAiS
`
`cowpsison may now be mddo between
`otolo-.esl-mmatrr carbon atoms ilk
`ho
`
`he o1iioal
`crars and
`
`lotarions ol
`l.L
`
`thc
`
`sp-mding rotations in the nIethl-1 gk ce Tic hot powi
`
`115 rorat-ir power 01
`wei nv g1ocoside
`tires
`
`tro-
`hat
`is
`the udtvidaI 0svunetrIc CLLIbCll 011115 in the
`tie corre-
`grc.ai in than tIe rotctoiy 11ovcr of
`the sugals This indnsi Ifs thai tIi s-iilsI 110 liOnel
`N5 000
`
`Ilrev i1d
`
`vrti
`
`t1- II
`
`t-o.
`
`1PR2014-01126- Ex 1023
`
`

`
`bureau
`
`tanJard Jounwi of 1vaeecch
`
`i-
`
`i-
`
`ft
`
`122-- Li
`
`by methyl group afFects the rot ations of all the asvnimetric
`bzi atonis in the sugar Tius c-oncept
`in agreement with
`is riot
`the rigid application of Hudsons second rule of iorotition Accord.
`eg to that rule the rotation of an amethyl glveoside of
`iSLigal
`is
`vdi ha
`-- 0M4 and
`that of
`the alpha fouii of
`the parent
`sugar
`bunJ
`itli
`11111 en
`hi ni
`liii
`there are several marked exceptions
`alue but
`fairly constant
`which were notcu by Hudson
`hcw deviu.1 ions
`An explanation of
`can be derived from the values for the optical
`rotatory power of
`the
`rums asymmetric carbon atoin in the sugars and glycosidos
`the difference in
`i.cc..rding to the theory of optrra superposi1oii
`rotations between the methyl gicosides
`inokeuLir
`and the eoi.re
`3p0111iflg sugars is given by the folkwhig ttc1uatiori
`.2 1241 R4
`-l9
`a14
`114 J.
`GOH rI-
`inee the vsjunes of 11 are larger than the values of 11 the value of
`will ai slightly with the structure of
`the sugar
`the case of arabhrose the sugar whjcti differed moei
`the equation
`the values of
`being of
`like oign and the values of
`results in all
`being different tins gives tile maxuiluril deviation from tire true valua
`of a.a0
`iota han ol the
`in abic
`the ve.lucs for the difference in niolcenlar
`a0 sre conipa red with the
`ziycon lcs nd sugar
`ilmlson
`from the vant Hoff cutuati.on
`The value of a-a as obtained from
`Cn.-flS obtained
`2a4 2cr..11
`anproxi
`
`.li
`
`vtlues of
`
`macely 10000
`
`IU.tLir
`
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`
`eu
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`
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`
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`
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`tO OsgnrOi
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`
`5$ rn LOtS Li
`
`lot pouto
`
`1PR2014-01126- Ex 1023
`
`10
`
`

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`it
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`Loll C01 flhit
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`0tC1Pii Chit
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`aie ObtIluled by c0011flCIOZ lLU Cocos
`liLa s.i
`TFE PREDICTIOIJ OF V..LUES FOIC TIE ROTATION Of UNO.N
`sUGAri.s ANE GUIICOSIDES
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`ildoooo xieo-
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`..etoriens
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`
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