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Chemistry of Natural Compounds

, Volume 19, Issue 4, pp 440–444 | Cite as

Transformation of the aglycones in steroid glycosides. 1. Synthesis of 20β-acetoxy-16β,23-epoxy-21,24-dinor-5α-cholane-3β,17α-diol 3-0-[0-β-D-glucopyranosyl-(1 → 2)-0-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside]

  • K. K. Koskoev
  • A. P. Shchelochkova
  • I. G. Reshetova
  • A. V. Kamernitskii
  • V. S. Bogdanov
Article

Abstract

The pathways of the chemical transformation of aglycones and their glycosides that do not affect the glycosidic chain are considered. Starting from 3β-hydroxy-5α-pregn-16-en-20-one 3-0-[0-β-D-glucopyranosyl-(1 → 2)-0-β-D-glucopyranosyl-(1 → 4)-β-D-galactopyranoside] the corresponding 16α(H),17α(OH)-dihydropyranone glycoside has been obtained. The latter has been converted into the polyacetate of a glycoside with a 17α,20β-dihydroxytetrahydropyran ring E. The structure and stereochemistry of the final compound have been shown from the results of the1H and13C NMR spectra and mass spectra.

Keywords

DMFA Ethyl Formate Steroid Glycoside Sodium Tetrahydroborate Bufadienolides 

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Copyright information

© Plenum Publishing Corporation 1984

Authors and Affiliations

  • K. K. Koskoev
  • A. P. Shchelochkova
  • I. G. Reshetova
  • A. V. Kamernitskii
  • V. S. Bogdanov

There are no affiliations available

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