Cyclization reactions of N1-(glycopyranosylamino) guanidines

Z. Györgydeák, Wolfgang Holzer, Joachim Thiem

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Acetylation of N1-(aldopyranosylamino)guanidines 2-4 with D-gluco, D-galacto, and L-arabino configuration gives rise to N1-per(O-acetylglycopyranosylamino)-N1,N2,N3-triacetylguanidines 5-7 in good yields, as already stated by Feather and coworkers [Carbohydr. Res., 267 (1995) 17-25] for the gluco compound. The acylaminoguanidines prepared have been cyclized under mild conditions (boiling in ethanol or treatment with cold 0.1 M sodium methylate solution) to afford 3-amino-N1-glycopyranosyl-5-methyl-1H-1,2,4-triazoles. The structure of these pyranosyl nucleosides 9, 10, 12-14 is discussed using 1H and 13C NMR spectroscopy and mass spectrometry.

Original languageEnglish
Pages (from-to)229-235
Number of pages7
JournalCarbohydrate Research
Volume302
Issue number3-4
DOIs
Publication statusPublished - Aug 7 1997

Fingerprint

Guanidines
Acetylation
Feathers
Cyclization
Nucleosides
Boiling liquids
Nuclear magnetic resonance spectroscopy
Mass spectrometry
Mass Spectrometry
Ethanol
Magnetic Resonance Spectroscopy
Sodium
1,2,4-triazole
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy

Keywords

  • 1,2,4-Triazole-nucleosides
  • Acetylated glycopyranosylaminoguanidines
  • Aminoguanidine

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Cyclization reactions of N1-(glycopyranosylamino) guanidines. / Györgydeák, Z.; Holzer, Wolfgang; Thiem, Joachim.

In: Carbohydrate Research, Vol. 302, No. 3-4, 07.08.1997, p. 229-235.

Research output: Contribution to journalArticle

Györgydeák, Z. ; Holzer, Wolfgang ; Thiem, Joachim. / Cyclization reactions of N1-(glycopyranosylamino) guanidines. In: Carbohydrate Research. 1997 ; Vol. 302, No. 3-4. pp. 229-235.
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