Tetrahedron

Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose

D Cicero, O Varela, RM De Lederkremer

Index: Cicero, Daniel; Varela, Oscar; De Lederkremer, Rosa M. Tetrahedron, 1990 , vol. 46, # 4 p. 1131 - 1144

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Citation Number: 21

Abstract

The synthesis of pyranoid and furanoid derivatives of 6-deoxy-4-thio-D-galactose from methyl α-D-glucopyranoside (1) is described. A key intermediate for the synthesis, methyl 2, 3-di-O-benzoyl-6-deoxy-4-thio-α-D-galactopyranoside (15) was prepared by different approaches from 1. Regioselectivity for the protection or modification of the hydroxyl groups of 1 or its derivatives was achieved by employing various reagents. The thiol group at C-4 ...