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New Method for Regioselective Glycosylation Employing Saccharide Oxyanions
Author(s) -
Matwiejuk Martin,
Thiem Joachim
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100861
Subject(s) - chemistry , glycosidic bond , regioselectivity , glycosylation , stereospecificity , stereochemistry , acceptor , glycosyl , glycosyl donor , combinatorial chemistry , organic chemistry , catalysis , biochemistry , enzyme , physics , condensed matter physics
As an alternative concept for glycosylation, the prior activation of acceptor hydroxy groups for selective glycosidic bond formation, was investigated to give complex oligosaccharides. Oxyanions obtained from partially protected saccharides were glycosylated by employing glycopyranosyl halides, and the regiochemical results were studied. Initially, partially methylated methyl‐α‐ D ‐glucopyranosides were used as a model system to study the underlying mechanistic principles of base‐promoted glycosylation. High regioselectivities and stereospecific glycosidic bond formations were achieved, and the scope of the methodology was extended with different perbenzylated glycosyl donors.