Stereoseleetive Synthesis of β-Mannopyranosides via the Temporary Silicon Connection Method

摘要

Increasing interest in the synthesis of biologically significant carbohydrate glycosides and conjugates has led to the development of ever more selective methods for the control of stereochemistry at the anomeric center. The stereospecific formation of β-mannopyranosides has proved particularly difficult to achieve, however, in spite of considerable effort, because the vicinal cis (axial) β-hydroxyl group blocks access to the β-face. The presence of the β-mannopyranoside entity, inter alia, in the core region of N-linked glycoproteins (cf. Figure 1) warrants significant attention toward its construction.