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Issue 27, 2014
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Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates

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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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Publication details

The article was received on 08 Apr 2014, accepted on 08 May 2014 and first published on 09 May 2014


Article type: Communication
DOI: 10.1039/C4OB00741G
Citation: Org. Biomol. Chem., 2014,12, 4816-4819
  • Open access: Creative Commons BY-NC license
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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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