Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 41, Pages 10972-10982Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901119
Keywords
carbohydrates; glycosylation; neighboring-group effects; stereoselectivity; substrate concentration
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Funding
- National Science Council, Taiwan [96-2113m-009-016]
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This study develops an operationally easy, efficient, and general 1,2-trans beta-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 beta-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosylsubstrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2-trans beta-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2-trans beta-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant beta-(1 -> 6)-glucan trisaccharide, beta-linked Gb(3) and isoGb(3) derivatives.
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