METHOD FOR PRODUCING 1-HYDROXYLATED VITAMIN D COMPOUND

摘要

PURPOSE: To provide a method for producing a 1-hydroxylated vitamin D compound, capable of obtaining the compound useful as an important intermediate for physiologically active vitamin D derivatives in a high yield and in a highly stereoselectivity. ;CONSTITUTION: A 1-unsubstituted-3-tetrahydropyranyloxy-5,6-trans vitamin D compound of formula I [R is hydroxymethyl which may, if necessary, be protected, hydrocarbylsulfonyloxy-(1-6C)alkyl, group of formula II (R₁, R₄ are H, OH, protected OH, or R¹ and R⁴ together represent a C=C; R₃ is H, 1-6C alkyl); THP is tetrahydropyranyl] is oxidized with selenious acid in the presence of a cooxidizing agent such as a tertiary amine oxide to obtain a 1α-hydroxy-3- tetrapyranyloxy-5,6-trans vitamin D compound of formula III. The compound of formula III is isomerized by the irradiation of UV light and, if necessary, subsequently subjected to the removal of the existing protecting group to obtain a 1α-hydroxy-3-tetrahydropyranyloxy-5,6-cis vitamin D compound or 1α- hydroxy-5,6-cis vitamin D compound.;COPYRIGHT: (C)1995,JPO