Process for steroidal peracyl glycosides

Details Process for steroidal peracyl glycosides Process for steroidal peracyl glycosides

C - Chemistry, Metallurgy

07

J

C07J 71/00 (2006.01) C07J 17/00 (2006.01)

Patent

CA 2138042

A process for the synthesis of 1-O-steroidal-peracyl-.beta.-glycosides that provides greater .beta.-anomeric selectivity with reduced by-products and side reactions. The process comprises reacting heptaacyl-D-cellobiosyl-1-halide, tetraacyl-D-glucosyl-1-halide or tetraacyl-D-galactosyl-1-halide and a trisubstituted silyl-3-O-steroid, wherein the steroid is tigogenin, hecogenin, 11-ketotigogen- in, diosgenin, or cholesterol, in the presence of zinc fluoride under suitable conditions. Typically, the halide is bromide, chloride or fluoride, the acyl is alkanoyl(C1-C6), benzoyl or toluoyl and the silyl substitution is alkyl(C1-C6), phenyl or phenyl al- kyl(C1-C6).

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