1320208-25-0

Basic information

• Product Name: (S)-2-(3-(methylthio)phenyl)-2-(trifluoromethyl)oxirane
• Synonyms: (S)-2-(3-(methylthio)phenyl)-2-(trifluoromethyl)oxirane
• CAS NO: 1320208-25-0
• Molecular Weight: 234.242
• Mol File: 1320208-25-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-2-(3-(methylthio)phenyl)-2-(trifluoromethyl)oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(3-(methylthio)phenyl)-2-(trifluoromethyl)oxirane(1320208-25-0)
• EPA Substance Registry System: (S)-2-(3-(methylthio)phenyl)-2-(trifluoromethyl)oxirane(1320208-25-0)

Safety Data

• Hazardous Substances Data: 1320208-25-0(Hazardous Substances Data)

Upstream product

• 128312-11-8 3-methylthiophenylboronic acid 
• 1320208-23-8 methyl(3-(3,3,3-trifluoroprop-1-en-2-yl)phenyl)sulfane 
• 1320208-24-9 (S)-3,3,3-trifluoro-2-(3-(methylthio)phenyl)propane-1,2-diol 

Relevant articles and documents

Synthesis of potent and orally efficacious 11β-hydroxysteroid dehydrogenase type 1 inhibitor HSD-016

Cortisol and the glucocorticoid receptor (GR) signaling pathway has been linked to the development of diabetes and metabolic syndrome. In vivo, 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) catalyzes the conversion of inactive cortisone to its active form, cortisol. Existing clinical data have supported 11β-HSD1 as a valid therapeutic target for type 2 diabetes. In our research program, (R)-1,1,1-trifluoro-2-(3-((R)-4-(4-fluoro-2- (trifluoromethyl)phenyl)-2-methylpiperazin-1-ylsulfonyl)phenyl)propan-2-ol (HSD-016) was discovered to be a potent, selective, and efficacious 11β-HSD1 inhibitor and advanced as a clinical candidate. Herein, a reliable and scalable synthesis of HSD-016 is described. Key transformations include an asymmetric synthesis of a chiral tertiary alcohol via Sharpless dihydroxylation, epoxide formation, and subsequent mild reduction. This route ensured multikilogram quantities of HSD-016 necessary for clinical studies.