Glucosylation of Some Steroidal 17-Hydroxy Derivatives

Author:

Černý Ivan,Pouzar Vladimír,Drašar Pavel,Havel Miroslav

Abstract

Eight 17-monoglucosides derived from androst-5-ene-3,17-diol, 14β-androst-5-ene-3,17-diol, 5β-androstane-3,17-diol and estradiol derivatives differing in configuration in the positions 17 and 3, have been prepared. The silver silicate - catalyzed glycosylation with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide gave 43-72% of the corresponding peracetylated β-D-glucopyranosides. The starting selectively protected 5β-androstane-3,17-diol derivatives were synthesized by a procedure utilizing orthogonality of the pivalate, acetate and nitrate protecting groups.

Publisher

Institute of Organic Chemistry & Biochemistry

Subject

General Chemistry

Cited by 8 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. ChemInform Abstract: Steroids. Part 362. Glucosylation of Some Steroidal 17-Hydroxy Derivatives.;ChemInform;2010-08-22

2. Etienic etienate as synthon for the synthesis of steroid oligoester gelators;Steroids;2005-08

3. The glycosylation of steroids;Tetrahedron;2004-06

4. Silver Silicate;Encyclopedia of Reagents for Organic Synthesis;2004-04-15

5. Synthesis of Linear Steroid Oligoesters Based on Etienic Acid;Collection of Czechoslovak Chemical Communications;2002

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