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Synthesis and properties of fused tetracyclic derivatives of 1,4-naphthoquinone thioglycosides

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Abstract

A series of 1,4-naphthoquinone O-acetylthioglycosides have been synthesized by the condensation of fully O-acetylated derivatives of 1-thio-d-xylose, 1-thio-L-arabinose, 1-thio-d-galactose, 1-thio-d-mannose, and 1-thiomaltose with 3-chloro-2-methoxy-1,4-naphtho-quinone. Their deacetylation with MeONa/MeOH proceeded with simultaneous heterocyclization to yield linear carbohydrate-containing tetracyclic quinones. Tetracycles with trans junction of the carbohydrate and quinone rings are poorly soluble in water and organic solvents.

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Authors and Affiliations

  1. Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, 159 prosp. 100-letiya Vladivostoka, 690022, Vladivostok, Russian Federation

    S. G. Polonik & V. A. Denisenko

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  1. S. G. Polonik
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  2. V. A. Denisenko
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Correspondence to S. G. Polonik.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1034–1038, May, 2009.

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Polonik, S.G., Denisenko, V.A. Synthesis and properties of fused tetracyclic derivatives of 1,4-naphthoquinone thioglycosides. Russ Chem Bull 58, 1062–1066 (2009). https://doi.org/10.1007/s11172-009-0135-y

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  • DOI: https://doi.org/10.1007/s11172-009-0135-y

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