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Coupling ofN-tosylhydrazones with tetrazoles : synthesis of 2-β-d-glycopyranosylmethyl-5-substituted-2H-tetrazole type glycomimetics

Kaszás, Tímea ; Cservenyák, Ivett ; Juhász-Tóth, Éva ; Kulcsár, Andrea E. ; Granatino, Paola ; Nilsson, Ulf J. LU ; Somsák, László and Tóth, Marietta (2021) In Organic and Biomolecular Chemistry 19(3). p.605-618
Abstract

Coupling reactions ofO-peracylated 2,6-anhydro-aldose tosylhydrazones (C-(β-d-glycopyranosyl)formaldehyde tosylhydrazones) with tetrazoles were studied under metal-free conditions using thermic or microwave activation in the presence of different bases. The reactions proved highly regioselective and gave the corresponding, up-to-now unknown 2-β-d-glycopyranosylmethyl-2H-tetrazoles in 7-67% yields. The method can be applied to get new types of disaccharide mimetics, 5-glycosyl-2-glycopyranosylmethyl-2H-tetrazoles, as well. Galectin binding studies withC-(β-d-galactopyranosyl)formaldehyde tosylhydrazone and 2-(β-d-galactopyranosylmethyl)-5-phenyl-2H-tetrazole revealed no significant inhibition of any of these lectins.

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author
; ; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Organic and Biomolecular Chemistry
volume
19
issue
3
pages
14 pages
publisher
Royal Society of Chemistry
external identifiers
  • scopus:85100236189
  • pmid:33355586
ISSN
1477-0520
DOI
10.1039/d0ob02248a
language
English
LU publication?
yes
id
3a50b612-5401-468f-8242-fff839252249
date added to LUP
2021-02-12 08:17:13
date last changed
2024-04-03 23:51:21
@article{3a50b612-5401-468f-8242-fff839252249,
  abstract     = {{<p>Coupling reactions ofO-peracylated 2,6-anhydro-aldose tosylhydrazones (C-(β-d-glycopyranosyl)formaldehyde tosylhydrazones) with tetrazoles were studied under metal-free conditions using thermic or microwave activation in the presence of different bases. The reactions proved highly regioselective and gave the corresponding, up-to-now unknown 2-β-d-glycopyranosylmethyl-2H-tetrazoles in 7-67% yields. The method can be applied to get new types of disaccharide mimetics, 5-glycosyl-2-glycopyranosylmethyl-2H-tetrazoles, as well. Galectin binding studies withC-(β-d-galactopyranosyl)formaldehyde tosylhydrazone and 2-(β-d-galactopyranosylmethyl)-5-phenyl-2H-tetrazole revealed no significant inhibition of any of these lectins.</p>}},
  author       = {{Kaszás, Tímea and Cservenyák, Ivett and Juhász-Tóth, Éva and Kulcsár, Andrea E. and Granatino, Paola and Nilsson, Ulf J. and Somsák, László and Tóth, Marietta}},
  issn         = {{1477-0520}},
  language     = {{eng}},
  number       = {{3}},
  pages        = {{605--618}},
  publisher    = {{Royal Society of Chemistry}},
  series       = {{Organic and Biomolecular Chemistry}},
  title        = {{Coupling ofN-tosylhydrazones with tetrazoles : synthesis of 2-β-d-glycopyranosylmethyl-5-substituted-2H-tetrazole type glycomimetics}},
  url          = {{http://dx.doi.org/10.1039/d0ob02248a}},
  doi          = {{10.1039/d0ob02248a}},
  volume       = {{19}},
  year         = {{2021}},
}