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Coupling ofN-tosylhydrazones with tetrazoles : synthesis of 2-β-d-glycopyranosylmethyl-5-substituted-2H-tetrazole type glycomimetics
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- Kaszás, Tímea (author)
- University of Debrecen
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- Cservenyák, Ivett (author)
- University of Debrecen
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- Juhász-Tóth, Éva (author)
- University of Debrecen
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- (creator_code:org_t)
- 2021
- 2021
- English 14 s.
- In: Organic and Biomolecular Chemistry. - : Royal Society of Chemistry (RSC). - 1477-0520 .- 1477-0539. ; 19:3, s. 605-618
- Journal article (peer-reviewed)
Abstract
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- 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.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
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- art (subject category)
- ref (subject category)
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