Reactive pseudo-oligosaccharides as potential irreversible inhibitors for sugar-binding proteins: synthesis of the diastereoisomers of (3,4,6/5)-3,4-epoxy-6-(β-D-galactopyranosylthio)-5-hydroxycyclohexene

Article abstract of DOI:10.1016/0008-6215(90)84202-6

Reaction of (+/-)-(3/4,5,6)-4-bromo-5,6-epoxy-3-hydroxycyclohexene with 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranose, followed by treatment of the products with base under phase-transfer conditions and then acetylation, gave the hexa-acetates of the