Stereoselective Synthesis of Antifungal Agent threo-2-(2,4-Difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol (SM-8668)

Autor: Saji, Ikutaro, Tamoto, Katsumi, Tanaka, Yoshihiro, Miyauchi, Hiroshi, Fujimoto, Koji, Ohashi, Naohito
Zdroj: Bulletin of the Chemical Society of Japan; May 1994, Vol. 67 Issue: 5 p1427-1433, 7p
Abstrakt: The stereoselective synthesis of antifungal agent threo-2-(2,4-difluorophenyl)-3-methylsulfonyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol (SM-8668) is described. The key step is the selective synthesis of intermediate threo-2(2,4-difluorophenyl)-2-(1-substituted ethyl)oxirane. threo-2-(2,4-Difluorophenyl)-2-(1-methylthioethyl)oxirane was synthesized threo-selectively by the reaction of 1-(2,4-difluorophenyl)-2-methylthio-1-propanone with dimethyloxosulfonium methylide in a heterogeneous media consisting of a hydrophobic solvent and aqueous alkaline solution.
Databáze: Supplemental Index