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Report | Regular issue | Vol 24, No. 5, 1986, pp.1265-1269
Published online, 1st January, 1970
DOI: 10.3987/R-1986-05-1265
Lincomycin Analogues. II. Chain-extension of Methyl-6-aldehydo-3,4-O-isopropylidene-1-thio-β-D-galcto-1,5-pyranoside

Jean M. J. Tronchet and Mohamed A. M. Massoud*

*Pharmaceutical Chemistry Department, Faculty of Pharmacy, Mansoura University, Mansoura, Egypt

Abstract

Synthesis of methyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside and its β-anomer (3 and 4) from the 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl brormide via the isothiauronium salt in HMPT involved a considerable increase in the proportion of the α-anomer. Deacetylation of (3 and 4) with sodium methoxide yielded 5 and 6 respectively. Conversion of (6) into the corresponding 3,4-isopropylidene derivative (7) followed by oxidation with Collin reagent gave the aldehydo-sugar (8) which when reacted with a stabilised phosphorane led in excellent yield to the Z-unsaturated bromo-sugar (9).