Collect. Czech. Chem. Commun.
1992, 57, 362-374
https://doi.org/10.1135/cccc19920362
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
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.
