STEREOSELECTIVE SYNTHESIS OF ANTIFUNGAL AGENT METHYLSULFONYL-1-(1H-1,2,4-TRIAZOL-1-YL)-2-BUTANOL (SM-8668)

Authors
SAJI I TAMOTO K TANAKA Y MIYAUCHI H FUJIMOTO K OHASHI N
Citation
I. Saji et al., STEREOSELECTIVE SYNTHESIS OF ANTIFUNGAL AGENT METHYLSULFONYL-1-(1H-1,2,4-TRIAZOL-1-YL)-2-BUTANOL (SM-8668), Bulletin of the Chemical Society of Japan, 67(5), 1994, pp. 1427-1433
Citations number
11
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
67
Issue
5
Year of publication
1994
Pages
1427 - 1433
Database
ISI
SICI code
0009-2673(1994)67:5<1427:SSOAAM>2.0.ZU;2-4
Abstract
The stereoselective synthesis of antifungal agent 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. -(2,4-Difluorophenyl)-2-(1-methylthioe thyl)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.