PRODUCTION OF 1ALPHA,25-DIHYDROXYVITAMINS D4 AND D7

摘要

PURPOSE: To obtain the subject compounds having differentiation-inducing activity and osteogenetic activity by converting a 22C alcohol derivative obtained from stigmasterol into a 5,7-diene modification via several processes followed by subjecting the 5,7-diene modification to ultraviolet-light irradiation and thermal isomerization successively. ;CONSTITUTION: A 22C alcohol derivative of formula I (Ph denotes phenyl) obtained from stigmasterol is tosylated and then treated with NaI to convert into a 22-iodine modification, which is then condensed with a sulfone derivative of formula II (R₁ is methyl or H; R₂ is H or methyl; Et denotes ethyl) to produce a 23-phenylsulfone derivative of formula III. This derivative is then subjected to reductive desulfurization followed by selectively α-epoxidize the double bond of the derivative of formula III, and the protecting group for the hydroxyl group of this compound is eliminated to convert into a diol compound followed by reducing the epoxy group of the diol compound to change into a triol compound, which is, in turn, subjected to ultraviolet-light irradiation and thermal isomerization successively, thus obtaining the objective 1α,25- dinydroxyvitamins D₄ and D₇ of formula IV.;COPYRIGHT: (C)1995,JPO