β-Acarbose. VI The Synthesis of a Hydroxylated Derivative of a Diastereoisomer of Acarbose

Abstract

A glycosyl bromide derived from an Nlinked carba disaccharide has been converted into a phenyl thioglycoside and condensed with benzyl 2,3,6,2′,3′,6′-hexa-O-benzyl-β-cellobioside to give an N-linked carba tetrasaccharide. Complete removal of protecting groups then gave the 6′′-hydroxylated derivative of β-acarbose, coined ‘β-adiposin-2’, a putative inhibitor of enzymes that process β-D-glucosidic linkages.