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

Wang, W.; Kong, F.

Angewandte Chemie 38(9): 1247-1250


ISSN/ISBN: 1521-3773
PMID: 29711750
DOI: 10.1002/(sici)1521-3773(19990503)38:9<1247::aid-anie1247>3.0.co;2-j
Accession: 065194274

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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.