Issue 27, 2014
From the journal:

Organic & Biomolecular Chemistry

Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates†

S. Mandala  and  U. J. Nilsson*a  

* Corresponding authors

a Centre for Analysis and Synthesis, Department of Chemistry, Lund University, POB 124, Lund, Sweden
E-mail: ulf.nilsson@chem.lu.se

Abstract

Tri-isopropylsilyl thio-glycosides (TIPS S-glycosides) were synthesized through base promoted SN2 substitution of glycosyl halides with TIPS-SH or by Lewis acid promoted glycosylation of TIPS-SH with glycosyl acetates or p-methoxyphenyl glycosides. Various thioglycoside derivatives were obtained in high yields by one-pot fluoride-mediated de-silylation and thiol alkylation with alkyl halides or Michael acceptors of one common TIPS S-glycoside.

Graphical abstract: Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates

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Article information

DOI
https://doi.org/10.1039/C4OB00741G
Article type
Communication
Submitted
08 Apr 2014
Accepted
08 May 2014
First published
09 May 2014
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2014,12, 4816-4819

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Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates

S. Mandal and U. J. Nilsson, Org. Biomol. Chem., 2014, 12, 4816 DOI: 10.1039/C4OB00741G

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