Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Synthesis of Anomeric Methyl 6-O-(L-Mycarosyl)-β-D-glucosaminides and 4-O-(L-Mycarosyl)-β-D-mycaminosides
Shinkiti KotoKazuo YagoShonosuke ZenSatoshi Omura
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1973 Volume 46 Issue 12 Pages 3800-3804

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Abstract

Condensation of 3,4-O-carbonyl-2,6-dideoxy-3-C-methyl-L-ribohexopyranosyl chloride (III) with methyl 2-deoxy-2-(2,4-dinitroanilino)-β-D-glucopyranoside and the subsequent removal of blocking groups gave the anomeric isomers of methyl 6-O-(2,6-dideoxy-3-C-methyl-L-ribohexopyranosyl)-2-amino-2-deoxy-β-D-glucopy-ranoside (VIIa, VIIb). On the other hand, the condensation of III with methyl 3,6-dideoxy-3-(N-methylcarboethoxyamino)-2-O-p-phenylazobenzoyl-β-D-glucopyranoside (XI) followed by removal of the acyl groups and N-methylation afforded the anomeric forms of methyl 4-O-(2,6-dideoxy-3-C-methyl-L-ribohexopyranosyl)-3,6-dideoxy-3-dimethylamino-β-D-glucopyranoside (XVa, XVb).

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