2,3,4-Tri-~-methyl-~-galnctose was identified as its characteristic anilide derivative. After recrystallizatioii from absolute ethanol, the 11i.p. was 167-168". aluuZ. Calcd. for CI6HP3OIX:X, 4 . 7 . Found: S , 4.7. An X-ray diflraction patterii of the crystals \vas identical with t h a t of :til authentic specimen. Test for Reversion.-On paper chromatography of a solution of D-g:dactose xiid L-rhamnose in equimolar concentrations ivhich had been stibjectvd to the sanic conditions rolysis of okra tnucilage no oligosaccharide rvetl, sho.5 i.1g f liat the altlobioitroiiic acid IrolJ..;i.; of okra inucilagc i i not :i rcvcrsioii
for the altlobiouroriic acid. Paper chromatography in solvent D of a hydrolysate of a small amount of the reduced product showed the presence of two trimethylgalactoses antl a dimethylrhamnose. The inaiti quantity of the reduced sirup v a s remethylated aiid then hydrolyzed t o yield tetrnmethylgalactose, a trimethylgalactose and a dimethylrhantnose as showu by paper chromatography in solvents I1 antl E. Attempts to isolate these derivatives were UIISL:C~CSSful bccause of the small amounts presetit. By using the bromine osidatioii procedure described above, rhamnose was showti t o be a t the reducing eiid of component 111. Paper chromatography of a hydrolysate of completely methylated conipoiient 111 indicated the resence of a tlimcth!-lrhatiinose, :i tlitiieth~lga1:ict~iroiiicacirl :tntl t e t r a i n e t ~ i ~ - l ~ r l a c t o s e .
Characterization of Aldotriouronic Acids.-Bromitte ositlatioti of L: sninil anioutit of coniputiciit I I folio\\.(i l 11)- aciil l i ~ - ~ l r o l ~a i-i i~l i s11:~pcrcliroiii:ttogr:tljli~~(Jf tlie liyilrul~~\:itv Acknowledgment.--The authors wish to express iiit1ic:itctI tli:tt gcii:tcloyL-is ;it tlic rrtlticitii: cittl t r f tlii> tritheir thxiks to Dr. I,. IJough for supplying the auliaride siitce g:tl:ictow, l l ~iiig > i ) c i . i t o\iclizi.tl t o gxl:tt,thentic speciiiieri of ~ , ~ ~ , l - t r i - O - m e t l i y l - i ~ - g ~ ~ l ~ t ~ ~ t ~ ~ s e t o i i i c w i J , did I t ( J t a1ipc:tr 011 t l i v e ~ t r ~ ~ t i t : t ~ o of g r thi. ~ i i iIt!.-~ ~ a~iilitleusetl for X-rny cc)iri~xirisu~i.
[ C O K T R I n L v l I f ~ SFRC)X I ~ E F E S C ERESE:ctivc compound. The latter coinpoutid W:LS itletil ti>- tlcgr:itlation with phosphotus pctitachloride :is 1 - 1 n c t l i y l - 2 - l i ~ i ~ r o s ~ ~1-methyl-1 ~ r o p ~ l -propcti~~l ~nc~th:iricplio~~~hoii;ttc.
lowered the yield of cyclic product to Xiyo. hloreover :L n e w optically active compound was forrnetl yield. This new compound had a rotation and it gave analytical values in good agreement with the empirical forinula CeIll,04P. Its infrared spectrum has a band a t e'M)O CIII. - - I due t o 0-13 stretching vibrations. X medium band at 1710 c~ii:-~ is assigned to C-C stretching vibrations or :til :mociatctl ester group lic.cuuse C 0 stretching vibrations would be espected to give a stronger absorption bnnd. The strong :tbsorption band a t 1 2 2 c i ~ i . - ~with a n :hsorption h n c t on the shoulder a t 1Yi.i ciii: * is :issigned to stretchiiig T,ibr:iticms o f the 1' 0 group:j- a n t i :.I ' I iciii: is :tssigned'2"to the P-0-C linkage. Since the infrared spectrum of the optically active IZ = I ) and 2-iiiethyl-S-oxo-l,3-dioxa-2-phospliacycloheptane (I, I i and I-l d i c l ~ l o r ig~i lv~i i~q a inirturc. o f 8-chloro- structure of t l i c l i l ~ ~ r n ~ ~ h ~ ~ s ~ , h o r - l n ! c . t l ? : l n ~ ~ l i i ~ s ~ ~ l ~ ~ ctlil-1 hytlri)geli i:ieth:iiie])lic~s~)hc,llalc :tiit1 di-3CH C I 1 0 1 I ci rc I I cliloroetliyl ~ i i e t l i a n e ~ ~ l i o s ~ ~ l i t ~ ~ ~ : ~ t e . 0 CII; lieceutly' it was s h o ~ ~ that - i i D - ( - j-i',::-butanetliol :ind niet~innel,liosplionyl dichloricle in methylene chloride anti in the prrsence of pyridine gave a 7,jC'; yield of thc cyclic product -3,1,;,-triiiiethq.l--clxo1 ,:3-dios~t--3-pliosph:t~~yclope~it:~iie (I, I< a n c l I
