One-pot preparation and activation of glycosyl trichloroacetimidates: operationally simple glycosylation induced by combined use of solid-supported, reactivity-opposing reagents

By the combined use of solid -supported reactivity-opposing reagents, that is, basic PTBD and acidic Nafion(R)-SAC resins., sequential reactions consisting of glycosyl trichloroacetimidate formation and glycosylation can be effected in a one-pot operation startitiv front 1-O-unprotected sugars. The...

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Bibliographic Details
Published inTetrahedron letters Vol. 45; no. 21; pp. 4039 - 4042
Main Authors Oikawa, M, Tanaka, T, Fukuda, N, Kusumoto, S
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 17.05.2004
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PHASE
ACID
ENVIRONMENTALLY BENIGN
GLYCOSIDATIONS
DEHYDRATIVE GLYCOSYLATION
OLIGOSACCHARIDE SYNTHESIS
CHEMISTRY
CATALYST
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Summary:By the combined use of solid -supported reactivity-opposing reagents, that is, basic PTBD and acidic Nafion(R)-SAC resins., sequential reactions consisting of glycosyl trichloroacetimidate formation and glycosylation can be effected in a one-pot operation startitiv front 1-O-unprotected sugars. The solid-supported reagents can be introduced into the reaction vessel either sequentially or, more conveniently. in a 'one-shot' manner in comparable yields. (C) 2004 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2004.03.170