Migration of Deuterium to C-20 in the Rearrangement Reaction of 17α-Deuterated 5α-Pregnane-3α, 20α-diol Disulfate by Hot Acid Hydrolysis to 17α-Ethyl-17β-methyl-5α-androst-13 (14)-en-3α-ol

抄録

The mechanism of the hot acid hydrolysis of 5α-pregnane-3α, 20α-diol disulfate was studied with the substrate containing deuterium in the 17α position. About 75% of the isotopic atom was retained in the formation of 17α-ethyl-17β-methyl-5α-androst-13 (14)-en-3α-ol. The stereospecific migration of deuterium to ethyl side chain of the product is suggesting that the rearrangement proceeded mainly via concerted mechanism.