THE FIRST CHEMICAL SYNTHESIS OF 6-THIO-D-FRUCTOPYRANOSE VIA METHYL 6-BROMO-6-DEOXY-1,3-O-ISOPRO-PYLIDENE-alpha-D-FRUCTOFURANOSIDE AS A KEY INTERMEDIATE

摘要

Selective bromination of sucrose,followed by acetalation with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid,afforded methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-alpha-D-fructofuranoside (4).The first chemical synthesis of 6-thio-D-fructopyranose was accomplished from 4 through its 6-S-acetyl-6-thio derivative.