Influence of the Benzyloxycarbonyl Protective Group on Glycosylation with Mannopyranosyl Donors

Abstract

The perbenzyloxycarbonylation of D‐mannose, D‐glucose, and D‐galactose was achieved in high yield. In the mannose series, the selective removal of the anomeric benzyloxycarbonyl group followed by the activation of the anomeric position furnished, depending on the activation conditions, either a bromo glycosyl donor or a trichloroacetimidate donor. The trichloroacetimidate donor, protected by benzyloxycarbonyl groups, was used successfully for the synthesis of a disaccharide.

Keywords:

• Benzyloxycarbonyl
• Protective group
• Glycosylation