Coupling ofN-tosylhydrazones with tetrazoles : synthesis of 2-β-d-glycopyranosylmethyl-5-substituted-2H-tetrazole type glycomimetics
(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.
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/3a50b612-5401-468f-8242-fff839252249
- author
- Kaszás, Tímea ; Cservenyák, Ivett ; Juhász-Tóth, Éva ; Kulcsár, Andrea E. ; Granatino, Paola ; Nilsson, Ulf J. LU ; Somsák, László and Tóth, Marietta
- organization
- publishing date
- 2021
- 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}}, }