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Hydrogen Bond Mediated Aglycone Delivery: Synthesis of Linear and Branched α‐Glucans
Author(s) -
Yasomanee Jagodige P.,
Demchenko Alexei V.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201405084
Subject(s) - aglycone , trisaccharide , chemistry , hydrogen bond , glycosylation , glycosyl , stereochemistry , oligosaccharide , acceptor , stereoselectivity , steric effects , molecule , biochemistry , organic chemistry , glycoside , catalysis , condensed matter physics , physics
A Hydrogen bond mediated aglycone delivery (HAD) method was applied to the synthesis of α‐glucans, which are abundant in nature, but as targets represent a notable challenge to chemists. The synthesis of linear oligosaccharide sequences was accomplished in complete stereoselectivity in all glycosylations. The efficacy of HAD may diminish with the increased bulk of the glycosyl acceptor, and may be an important factor for the syntheses of oligomers beyond pentasaccharides. The synthesis of a branched structure proved more challenging, particularly with bulky trisaccharide acceptors.