Highly Regio- and Stereoselective Synthesis of Mannose-Containing Oligosaccharides with Acetobromo Sugars as the Donors and Partially Protected Mannose Derivatives as the Acceptors via Sugar Orthoester Intermediates

Angew Chem Int Ed Engl. 1999 May 3;38(9):1247-1250. doi: 10.1002/(SICI)1521-3773(19990503)38:9<1247::AID-ANIE1247>3.0.CO;2-J.

Abstract

An orthoester formation/rearrangement sequence, in which 1,2-O-ethylidenated mannose or partially protected mannosides function as the glycosyl acceptors and simple acetobromo sugars as the glycosyl donors (see reaction scheme), provides an efficient and highly regio- and stereoselective route to mannose-containing 1→6, 1→3, and 3,6-branched oligosaccharides with exclusive 1,2-trans linkage.

Keywords: Oligosaccharides; Protecting groups; Rearrangements; Synthetic methods.