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Synthesis of glucosides of 3-alk[en]yl-2-hydroxy-1,4-naphthoquinones

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Abstract

The condensation of D-glucose (tert-butyl orthoacetate) with 3-alk[en]yl-2-hydroxy-1,4-naphthoquinones has yielded a series of acetylated glycosides of hydroxynaphthoquinones. It has been established that the time of the glycosylation reaction lengthens with an increase in the length and in the degree of branching of the side chain of the quinone. It has been shown that when the glycosides obtained are deacetylated cleavage of the glycosidic bond takes place with the formation of glucose and the corresponding quinone methyl ethers. Details of IR and1H and13C NMR spectra are given.

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Authors
  1. S. G. Polonik
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  2. A. M. Tolkach
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  3. V. A. Denisenko
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  4. N. I. Uvarova
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Additional information

Pacific Ocean Institute of Bioorganic Chemistry, Far Eastern Scientific Center, Academy of Sciences of the USSR, Vladivostok. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 328–331, May–June, 1983.

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Polonik, S.G., Tolkach, A.M., Denisenko, V.A. et al. Synthesis of glucosides of 3-alk[en]yl-2-hydroxy-1,4-naphthoquinones. Chem Nat Compd 19, 310–313 (1983). https://doi.org/10.1007/BF00579767

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  • DOI: https://doi.org/10.1007/BF00579767

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