Synthesis of 2,3-di-O-glycosyl derivatives of methyl α- and β-D-glucopyranoside

Article abstract of DOI:10.1016/0008-6215(93)84002-N

The syntheses are described of 2,3-di-O-glycosyl derivatives of methyl α- and β-D-glucopyranoside having α-D-manno-, β-D-galacto, α-L-rhamno, α-L-fuco, and β-L-fuco-pyranosyl substituents at O-2 and O-3.The syntheses involved glycosylation of methyl 4,6-O-benzylidene-α- (24) and β-D-glucopyranoside (21), and substituted derivatives of 21 bearing 2-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-, -(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-, -(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-, and -(2,3,4-tri-O-benzoyl-β-L-fucopyranosyl) groups.