Please use this identifier to cite or link to this item: http://hdl.handle.net/10995/31832
Title: Synthesis of acyclic nucleoside analogues by one-step Vorbrüggen glyco-sylation of 1,2,4-triazolo[1,5-a]pyrimidine-7-ones
Authors: Khalymbadzha, I. A.
Deev, S. L.
Shestakova, T. S.
Rusinov, V. L.
Chupakhin, O. N.
Issue Date: 2015
Citation: Synthesis of acyclic nucleoside analogues by one-step Vorbrüggen glyco-sylation of 1,2,4-triazolo[1,5-a]pyrimidine-7-ones / I. A. Khalymbadzha, S. L. Deev, T. S. Shestakova, V. L. Rusinov, O. N. Chupakhin // Chimica Techno Acta. — 2015. — Vol. 2. № 2. — С. 158-160.
Abstract: New analogues of acyclovir have been prepared by reacting 1,2,4 -triazolo[1,5-a]pyrimidin-7-ones 1а-i and (2-acetoxyethoxy)methyl acetate 2 in the presence of trimethylsilyl trifluoromethanesulfonate as a catalyst. The interaction between the compounds 1а-е and 2 has led to a mixture of N3 and N4 isomers. In contrast, the reaction of compounds 1g-i and 2 proceeded selectively to form N3 isomers. In the case of compounds 1a-c the predominant product is the one with the acyclic moiety in azine ring (N4 isomer). Interaction between 1d-f and 2 has led to mixtures comprising mainly N3 isomer. It has been found that the ratio of glycosylation products 1 and 2 are thermodynamically controlled. The structure of the obtained compounds has been proved by 1Н, 13С, two-dimensional 1Н-13С NMR spectroscopy and X-ray analysis.
Keywords: ACYCLOVIR
АЦИКЛОВИР
URI: http://hdl.handle.net/10995/31832
RSCI ID: https://elibrary.ru/item.asp?id=23785881
ISSN: 2409-5613
Other versions: http://hdl.handle.net/10995/31833
DOI: http://dx.doi.org/10.15826/chimtech.2015.2.2.017
Origin: Chimica Techno Acta. 2015. Vol. 2. № 2.
Appears in Collections:Chimica Techno Acta

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