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

Mandal, Santanu LU and Nilsson, Ulf LU (2014) In Organic and Biomolecular Chemistry 12(27). p.4816-4819
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.
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author
and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic and Biomolecular Chemistry
volume
12
issue
27
pages
4816 - 4819
publisher
Royal Society of Chemistry
external identifiers
  • pmid:24867410
  • wos:000338118400003
  • scopus:84902775199
  • pmid:24867410
ISSN
1477-0539
DOI
10.1039/c4ob00741g
language
English
LU publication?
yes
id
0f787bdb-b588-44ef-8545-a72b56c785f6 (old id 4452417)
date added to LUP
2016-04-01 10:47:11
date last changed
2025-10-14 12:21:38
@article{0f787bdb-b588-44ef-8545-a72b56c785f6,
  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.}},
  author       = {{Mandal, Santanu and Nilsson, Ulf}},
  issn         = {{1477-0539}},
  language     = {{eng}},
  number       = {{27}},
  pages        = {{4816--4819}},
  publisher    = {{Royal Society of Chemistry}},
  series       = {{Organic and Biomolecular Chemistry}},
  title        = {{Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates.}},
  url          = {{http://dx.doi.org/10.1039/c4ob00741g}},
  doi          = {{10.1039/c4ob00741g}},
  volume       = {{12}},
  year         = {{2014}},
}