Synthesis of the methyl α-glycosides of some isomalto-oligosaccharides specifically deoxygenated at position C-4

Abstract

Methyl α-isomaltoside and methyl α-isomaltotrioside specifically deoxygenated at position C-4 of various glucopyranosyl units were synthesized by condensation of either 1,6-di- O-acetyl-2,3-di- O-benzyl-4-deoxy- α, β- d- xylo-hexopyranose (7) or 1,6-di- O-acetyl-2,3,4-tri- O-benzyl- α, β- d-glucopyranose (10) [mediated by silver perchlorate and tin(IV) chloride] with suitably blocked derivatives of methyl α-d-glucopyranoside, its 4-deoxy analog 6, or methyl 4′-deoxy α-isomaltoside (13), respectively.