4.5 Article

Activation of glycosyl trichloroacetimidates with perchloric acid on silica (HClO4-SiO2) provides enhanced α-selectivity

Journal

CARBOHYDRATE RESEARCH
Volume 345, Issue 14, Pages 2074-2078

Publisher

ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2010.07.030

Keywords

Glycosylation; Trichloroacetimidates; Stereoselectivity; Perchloric acid on silica

Funding

  1. NIH, NCI

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Obtaining high stereoselectivity in glycosylation reactions is often challenging in the absence of neighboring group participation. In this study, we demonstrate that activation of glycosyl trichloroacetimidate donors with immobilized perchloric acid on silica (HClO4-SiO2) provides higher alpha-selectivity than trimethylsilyl triflate (TMSOTf) for reactions that do not involve neighboring group participation. Published by Elsevier Ltd.

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