Collect. Czech. Chem. Commun. 1992, 57, 362-374

Glucosylation of Some Steroidal 17-Hydroxy Derivatives

Ivan Černý, Vladimír Pouzar, Pavel Drašar and Miroslav Havel

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


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.