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Synthesis of all of the possible stereoisomers of 4-benzamido-3-hydroxy-2-(δ-carbomethoxybutyl)thiophan

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The stereospecific synthesis of the four possible isomers of 4-benzamido-3-hydroxy-2-(δ-carbomethoxybutyl)thiophan (III–VI) was accomplished from 4-benzamido-3-oxo-2-(δ-carbomethoxybutylidene)thiophan (I) using the stereospecificity of the reduction of the oxo group of I, the stereospecificity of the reduction of the exocyclic double bond of 4-benzamido-3-hydroxy-2-(δ-carbomethoxybutylidene)thiophan (II), and inversion of the hydroxyl group of III and IV. The configurations of the stereoisomers obtained were established by PMR spectroscopy.

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Literature cited

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Authors and Affiliations

  1. All-Union Scientific-Research Vitamin Institute, Moscow

    S. D. Mikhno, T. M. Filippova, N. S. Kulachkina, T. N. Polyanskaya, I. M. Kustanovich & V. M. Berezovskii

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  1. S. D. Mikhno
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  2. T. M. Filippova
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  3. N. S. Kulachkina
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  4. T. N. Polyanskaya
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  5. I. M. Kustanovich
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  6. V. M. Berezovskii
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Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 897–901, July, 1972.

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Mikhno, S.D., Filippova, T.M., Kulachkina, N.S. et al. Synthesis of all of the possible stereoisomers of 4-benzamido-3-hydroxy-2-(δ-carbomethoxybutyl)thiophan. Chem Heterocycl Compd 8, 813–817 (1972). https://doi.org/10.1007/BF00475209

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  • DOI: https://doi.org/10.1007/BF00475209

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