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Analogs of pyrimidine nucleosides. 15. Synthesis of 3′-hydroxy- and 4′-hydroxyftorafur

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A method for the synthesis of ftorafur metabolites, viz., 3′-hydroxy- and 4′-hydroxyftorafur, from 3-benzoxytetrahydrofuran, which is chlorinated in the presence of UV irradiation, was developed. The resulting mixture of α-chloro ethers is alkylated by 2,4-bis(trimethylsilyl)-5-fluorouracil. The alkylation products are separated by fractional crystallization and column chromatography on silica gel, and the benzoyl protective group is removed, cis-4′-Hydroxyftorafut, trans-3′-hydroxyftorafur, and cis-3′-hydroxyftorafur, which were identified from the PMR spectra and by comparison with the literature data, were obtained.

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Authors and Affiliations

  1. Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, 226006, Riga

    L. T. Kaulinya, R. A. Zhuk & M. Yu. Lidak

Authors
  1. L. T. Kaulinya
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  2. R. A. Zhuk
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  3. M. Yu. Lidak
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Additional information

See [1] for Communication 14.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1094–1096, August, 1981.

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Kaulinya, L.T., Zhuk, R.A. & Lidak, M.Y. Analogs of pyrimidine nucleosides. 15. Synthesis of 3′-hydroxy- and 4′-hydroxyftorafur. Chem Heterocycl Compd 17, 813–815 (1981). https://doi.org/10.1007/BF00503665

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  • DOI: https://doi.org/10.1007/BF00503665

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