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

Summary, in English

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.

• Author: Santanu Mandal; Ulf Nilsson
• Department/s: Centre for Analysis and Synthesis
• Publishing year: 2014
• Language: English
• Pages: 4816-4819
• Publication/Series: Organic and Biomolecular Chemistry
• Volume: 12
• Issue: 27
• Links: http://dx.doi.org/10.1039/c4ob00741g
• Document type: Journal article
• Publisher: Royal Society of Chemistry
• Topic: Chemical Sciences
• Status: Published
• ISBN/ISSN/Other: ISSN: 1477-0539