Effect of complexation of silver ion with the glycosyl donor and acceptor on the regio- and stereo-selectivity in the β-mannopyranosylation of 1,3-di-N-benzyloxycarbonyl-2-deoxystreptamine using silver triflate as a promoter in tetrahydrofuran

Article abstract of DOI:10.1016/0008-6215(90)84045-V

A pseudodisaccharide, a 5-O-(β-D-mannopyranosyl)-2-deoxystreptamine derivative, was obtained preferentially when 2,3,4-tri-O-allyl-6-O-benzyl-α-D-mannopyranosyl chloride (1) was used as the glycosyl donor for coupling with 1,3-di-N-benzyloxycarbonyl-2-deoxystreptamine (2) using silver triflate as a promoter in tetrahydrofuran.Complexation of the glycosyl acceptor and the allyl protecting group of the glycosyl donor with the promoter proved important for the regio- and stereo-selective formation of the β-mannopyranosyl linkage.