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Low‐Concentration 1,2‐ trans β‐Selective Glycosylation Strategy and Its Applications in Oligosaccharide Synthesis
Author(s) -
Chao ChinSheng,
Li ChenWei,
Chen MinChun,
Chang ShihSheng,
Mong KwokKong Tony
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901119
Subject(s) - glycosylation , trisaccharide , chemistry , glycosidic bond , oligosaccharide , glycosyl , carbohydrate chemistry , glycosyl donor , stereochemistry , combinatorial chemistry , biochemistry , enzyme
This study develops an operationally easy, efficient, and general 1,2‐ trans β‐selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent β‐selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of their structures and hydroxyl‐protecting functions. This low‐concentration 1,2‐ trans β‐selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2‐ trans β‐glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant β‐(1→6)‐glucan trisaccharide, β‐linked Gb 3 and isoGb 3 derivatives.