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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
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
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
2014-06-18 14:49:34
date last changed
2017-01-01 03:53:46
@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},
  volume       = {12},
  year         = {2014},
}