Carbohydrate Research p. 229 - 235 (1997)
Update date:2022-09-26
Topics:
Gyoergydeak, Zoltan
Holzer, Wolfgang
Thiem, Joachim
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.
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