synthesis of acyclic nucleoside analogues based on 1,2,4-triazolo[1,5-a]pyrimidine-7-ones by one-step vorbrüggen glycosylation

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ID: 229786
2015
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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. Thei nteraction 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.
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khalymbadzha2015chimicasynthesis Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors I. A. Khalymbadzha, S. L. Deev, T. S. Shestakova, V. L. Rusinov, O. N. Chupakhin
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Journal archives of agronomy and soil science
Year 2015
DOI
10.15826/chimtech.2015.2.2.017
URL
https://journals.urfu.ru/index.php/chimtech/article/view/1126
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