By Sidney M. Cantor
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Additional info for Advances in Carbohydrate Chemistry and Biochemistry, Vol. 7
62) P. A. Levene and J. Compton, J . Biol. ] 20 R. A. LAIDLAW AND E. 0. V. PERCIVAL HOHC 'q0>Hl I Me 0, :qoy OH MeOHC ,o OMe ,o Me 0 , Je CMet CMe, LIV LV OH MeOHC Hqo$H, OH OH LVI The product gave 5-methyl-~-rhamnose phenylosazone and formed a furanoside, but not a pyranoside, with methanolic hydrogen chloride. 5. d,S-DimethyL~-rhamnose was converted into Methyl 2,3-isopropylidene-a-~-rhamnopyranoside the 4-tosyl derivative (LVII), from which the isopropylidene residue was removed by mild hydrolysis.
N. Jones, J . Chem. ,1125 (1950). 21 METHYL ETHERS ment with phenylhydrazine acetate gave a monomethyl-L-rhamnose phenylosazone, thus proving substitution on C2. 6. e6-86 H Me H OMe OMe OAc LXIII The constitution of the product was proved by methylation to give methyl 2,3,4-trimethyl-/3-~-rhamnopyranoside, from which trimethy1-Lrhamnopyranose and the crystalline 2,3,4-trimethyl-~-rhamnonolactone, rapidly hydrolyzed in water, were obtained. 06 LXII 7. d,S,4-Trimethyl-~-rhamnose Trimethyl-L-rhamnopyranose has been isolated from methylated gum arabic on hydrolysis, and from the specific somatic polysaccharide of M.
L. Hirst and 5. Peat, J . Chem. , 1983 (1937). ) HzO 14, 78 -+ (78) H. D. K. Drew, E. H. Goodyear and W. N. Haworth, J . Chem. , 1237 (1927). (79) W. N. Haworth and C. W. Long, J . Chem. ,345 (1929). 30 R. A. LAIDLAW AND E, Q. V. PERCNAL TABLEI I1 The Methyl Ethers of D-Arabinose Substance Melting point, "C. 2 -, amide 2,4-Dimethyl-carabinose lactone - 27, 34,40 34 27 40 40 34 41 42 41 41 35 -, t208 - 131 Sirup 163 117 sirup -, smide 2,3-Dimethyl-~-arabinose -, anilide 2,3-Dimethyl-~-arabonic acid -, lactone -, amide 2,5-Dimethyl-carabinose 2,5Dimethyl-~-arabonicacid References point, "C 132 sirup 139 158 ' 3irup - 30 132 I63 iirup limp limp !
Advances in Carbohydrate Chemistry and Biochemistry, Vol. 7 by Sidney M. Cantor