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Synthesis and applications of a light-fluorous glycosyl donor

Zhang, F and Zhang, W and Zhang, Y and Curran, DP and Liu, G (2009) Synthesis and applications of a light-fluorous glycosyl donor. Journal of Organic Chemistry, 74 (6). 2594 - 2597. ISSN 0022-3263

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Abstract

A new method using a light-fluorous glycosyl donor and an orthogonal tagging strategy to synthesize oligosaccharides and glycoconjugates has been developed. The glycosyl donor orthogonally protected with a C F -Silyl tag and benzoyl groups was reacted with excess amounts of glycosyl acceptor. Fluorous solid-phase extraction separated the glycosylated product and unreacted glycosyl acceptor. This new protocol has high reaction efficiency and easy separation, which was demonstrated in the synthesis of an unprotected trisaccharide and an O-glycosylated serine in this paper. © 2009 American Chemical Society. 8 17


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Zhang, F
Zhang, W
Zhang, Y
Curran, DPcurran@pitt.eduCURRAN
Liu, G
Date: 20 March 2009
Date Type: Publication
Journal or Publication Title: Journal of Organic Chemistry
Volume: 74
Number: 6
Page Range: 2594 - 2597
DOI or Unique Handle: 10.1021/jo9000993
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0022-3263
MeSH Headings: Glycoconjugates--chemical synthesis; Glycosylation; Methods; Oligosaccharides--chemical synthesis; Solid Phase Extraction
Other ID: NLM NIHMS140858, NLM PMC2754202
PubMed Central ID: PMC2754202
PubMed ID: 19216499
Date Deposited: 27 Feb 2013 15:53
Last Modified: 02 Apr 2021 22:55
URI: http://d-scholarship.pitt.edu/id/eprint/17501

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