Abstract
The by-products formed in the preparation of strophanthiodol 19-rhamnoside and 3, 19-bisrhamnoside by the orthoester method are 3β,5-dihydroxy-8,19-epoxy-5β,14β, 17α-card-20(22)-enolide and its 3-α-L-rhamnoside. 3β,5-Dihydroxy-8,19-epoxy-5β, 14α,17β-card-20(22)-enolide has been obtained by the action of a solution of HBr in nitromethane on strophanthidol.
Similar content being viewed by others
Literature cited
N. Sh. Pal'yants and N. K. Abubakirov, Khim. Prir. Soedin., 125 (1977).
T. Kubota and M. Ehrenstein, J. Org. Chem.,29, 342 (1964).
K. Tori and K. Aono, Annu. Rep. Shionogi Res. Lab.,15, 130 (1965).
F. Burkhardt, W. Meier, A. Fürst, and T. Reichstein, Helv. Chim. Acta,50, 607 (1967).
W. Klyne, Biochem. J.,47, No. 4, xli (1950).
A. A. Akimaliev, N. Sh. Pal'yants, N. K. Alimbaeva, and N. K. Abubakirov, Khim. Prir. Soedin., 668 (1979).
W. Merkel and M. Ehrenstein, Helv. Chim. Acta,52, 2156 (1969).
A. Ya. Khorlin, A. F. Bochkov, and N. K. Kochetkov, Khim. Prir. Soedin., 6 (1966).
M. Mazurek and A. S. Perlin, Can. J. Chem.,43, 1918 (1965).
V. T. Chernobai, Zh. Obshch. Khim.,34, 3852 (1964).
Additional information
Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 744–750, November–December, 1981.
Rights and permissions
About this article
Cite this article
Pal'yants, N.S., Abubakirov, N.K. Glycosylation of cardenolides. VIII. Structures of the by-products of the synthesis by the orthoester method of strophanthidol rhamnosides. Chem Nat Compd 17, 540–545 (1981). https://doi.org/10.1007/BF00574373
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/BF00574373