Glycosylation using unprotected alkynyl donors

Mamidyala, Sreeman K. and Finn, M. G. (2009) Glycosylation using unprotected alkynyl donors. Journal of Organic Chemistry, 74 21: 8417-8420. doi:10.1021/jo901857x

Author Mamidyala, Sreeman K.
Finn, M. G.
Title Glycosylation using unprotected alkynyl donors
Journal name Journal of Organic Chemistry   Check publisher's open access policy
ISSN 0022-3263
Publication date 2009-11-06
Sub-type Article (original research)
DOI 10.1021/jo901857x
Volume 74
Issue 21
Start page 8417
End page 8420
Total pages 4
Place of publication Washington, DC, United States
Publisher American Chemical Society
Language eng
Formatted abstract
Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in acetonitrile with 5% AuCl3 for reaction with various primary alcohol acceptors, the latter used in 10-fold molar excess relative to donor. Donors containing the 2-butynyl group were more reactive, giving good yields of glycoside products at lower temperatures. Secondary alcohols could also be used but with diminished efficiency. The propargylic family of donors is especially convenient because they can be easily prepared on large scale by Fischer glycosylation and stored indefinitely before chemoselective activation by the catalyst.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: ERA 2012 Admin Only
Institute for Molecular Bioscience - Publications
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Citation counts: TR Web of Science Citation Count  Cited 22 times in Thomson Reuters Web of Science Article | Citations
Scopus Citation Count Cited 23 times in Scopus Article | Citations
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Created: Sun, 30 Oct 2011, 10:50:45 EST by Sreeman Mamidyala on behalf of Institute for Molecular Bioscience