PMID: 9437794Jan 23, 1998Paper

Synthesis of cardenolide glycosides and putative biosynthetic precursors of cardenolide glycosides

Steroids
M LutaW Kreis

Abstract

A rapid and efficient procedure for glycosylation of steroids was established using a modified Koenigs-Knorr procedure. Peracetylated beta-glycosides were synthesized by reaction of cardenolides, various pregnanes and 23-nor-5,20(22)E-choldienic acid at room temperature with the peracetylated 1-bromo derivatives of D-glucose, D-galactose, D-fucose and cellobiose. Subsequent deprotection was performed by alkaline hydrolysis with sodium methoxide. Structures of the respective glycosides were established by NMR techniques. The complete protocol was shown to be non-destructive at all stages to the sugar moiety and the steroidal nucleus. The gamma-unsaturated lactone ring of the cardenolides was shown to remain intact and no formation of C-14 unsaturated compounds was observed.

References

Feb 1, 1996·Glycoconjugate Journal·D M Whitfield, S P Douglas

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Citations

Jun 6, 2007·Biotechnology Letters·Cezary PaczkowskiZdzislaw A Wojciechowski
Dec 24, 2013·Phytochemistry·Mark S ButlerRonald J Quinn
Nov 8, 2011·The Journal of Organic Chemistry·Yuyong MaBiao Yu
Jul 19, 2008·Journal of Agricultural and Food Chemistry·Patrick L Selmair, Peter Koehler
Sep 12, 2007·Journal of Natural Products·Tian-Min WangShao-Qing Cai

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