4.4 Article

N-dimethylphosphoryl-protected glucosamine trichloroacetimidate as an effective glycosylation donor

Journal

TETRAHEDRON LETTERS
Volume 48, Issue 26, Pages 4557-4560

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.04.150

Keywords

dimethylphosphoryl; protecting group; glucosamine; trichloroacetimidate; glycosylation

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Glycosylation of a variety of alcohols with 3,4,6-tri-O-acetyl-2-N-dimethylphosphoryl-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate as a glycosyl donor provided the corresponding coupled products in high yields and good beta-selectivity. N-Dimethylphosphoryl-protection stayed stable under acidic and basic conditions for further elaboration of the glucosaminecontaining oligosaccharides. (c) 2007 Elsevier Ltd. All rights reserved.

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