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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
Author(s) -
Wang Wei,
Kong Fanzuo
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990503)38:9<1247::aid-anie1247>3.0.co;2-j
Subject(s) - mannose , orthoester , stereoselectivity , glycosyl , chemistry , stereochemistry , sugar , sequence (biology) , organic chemistry , biochemistry , catalysis
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.