The syntheses of 3 beta-steroidal diacylglyceryl sulfides, sulfoxides, and sulfones.

The syntheses of the diacylglyceryl-sulfide 4a, sulfoxide 4b, and sulfone 4c of dehydroepiandrosterone (3 beta-hydroxyandrost-5-en-17-one, DHEA, 1a) are described. Nucleophilic substitution of 1,2-dipalmitoyl-3-iodo-rac-3-deoxyglycerol (2) with 3 beta-mercaptoandrost-5-en-17-one (3) afforded the diacylglyceryl-sulfide (4). Selective oxidation of 4 with m-chloroperbenzoic acid gave the diacylglyceryl-sulfoxide 4b and diacylglyceryl-sulfone 4c of DHEA. The sulfide 4a was a very weak inhibitor of glucose-6-phosphate dehydrogenase, whereas the sulfone 4c did not inhibit the enzyme.