Abstract
The glycosylation of bis(trimethylsilyl) derivatives of uracil and thymine by bifunctionally modified derivatives of D-glucofuranose in the presence of SnCl4 as the condensing agent was studied. It is shown that the β anomers of D-glucofuranose derivatives with a 1,2-trans orientation of the OAc groups undergo condensation more readily than the α anomers. Both anomers give a mixture of α and β nucleosides with significant preponderance of the latter due to the primary formation of a 1,2-acetoxonium ion. It is assumed that the formation of α nucleosides is due to the competitive coparticipation of other groups and/or more remote acetyl groups.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 542–548, April, 1982.
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Mikhailopulo, I.A., Zaitseva, G.V. & Mikhailovskaya, N.A. Synthesis of bifunctionally modified hexofuranosides of thymine and uracil. Chem Heterocycl Compd 18, 417–423 (1982). https://doi.org/10.1007/BF00503567
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DOI: https://doi.org/10.1007/BF00503567