Sugar chemistry without protecting groups: a novel regioselective synthesis of 6-O-acyl-D-glucopyranoses and methyl-6-O-acyl-α--glucopyranosides
作者:Daniel Plusquellec、Krystyna Baczko
DOI:10.1016/s0040-4039(00)96390-1
日期:1987.1
hydroxyl groups of α--glucose and methyl-α--glucoside were selectively esterified by treating the free sugars with -acylthiazolidine-2-thiones, thus affording respectively 6--acyl--glucopyranoses and methyl-6--acyl-α--glucopyranosides in high yields. This new reaction is compared with our previous synthesis of 1--acyl-β--glucopyranoses from β--glucose and interpreted in terms of anomeric effect.