Journal of the Chemical Society. Perkin transactions I p. 1971 - 1977 (1980)
Update date:2022-08-05
Topics:
Charon, Daniel
Szabo, Ladislas
At pH 11.5 in 0.2M-sodium tetraborate solution and in the presence of Ni2+, 2-O-benzyl-D-arabinose reacts with oxaloacetic acid to give a 50-60percent yield of 5-O-benzyl-3-deoxyoct-2-ulosonic acids (mixed D-gluco- and D-manno-isomers).The methyl esters of these were separated and the α-methyl glycoside of the D-manno-isomer was prepared.The conformation of the compounds was established by n.m.r. spectroscopy at 250 MHz.It was observed that esterification of the carboxy-group greatly increases the stability of the glycosidic bond of 3-deoxy-D-manno-octulosonic acid while the benzyl substituent in position 5 exerts only a weak stabilising effect. 2-O-Benzyl-D-glyceraldehyde, when treated with oxaloacetic acid in the presence of Ni2+ at pH 7 in the absence of borate, yields 5-O-benzyl-3-deoxyhex-2-ulosonic acids, the predomonant D-erythro-isomer being isolated as its methyl ester.
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