1027190-58-4

Basic information

• Product Name: (2R,3R)-Oxirane-2,3-dicarboxylic acid 2-ethyl ester 3-pentafluorophenyl ester
• CAS NO: 1027190-58-4
• Molecular Weight: 326.177
• Mol File: 1027190-58-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3R)-Oxirane-2,3-dicarboxylic acid 2-ethyl ester 3-pentafluorophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-Oxirane-2,3-dicarboxylic acid 2-ethyl ester 3-pentafluorophenyl ester(1027190-58-4)
• EPA Substance Registry System: (2R,3R)-Oxirane-2,3-dicarboxylic acid 2-ethyl ester 3-pentafluorophenyl ester(1027190-58-4)

Safety Data

• Hazardous Substances Data: 1027190-58-4(Hazardous Substances Data)

Upstream product

• 74243-85-9 trans-2,3-bis(ethoxycarbonyl)oxirane 
• 771-61-9 2,3,4,5,6-pentafluorophenol 
• 93061-20-2 (-)-(2R,3R)-trans-Oxiran-2,3-dicarbonsaeure-monoethylester 

Relevant articles and documents

A convenient synthesis of optically pure (2R, 3R)-2, 3-epoxysuccinyl - Dipeptides

(2R,3R)-trans-Epoxysuccinyl-dipeptides (7a-7d) were synthesized by acylation of dipeptides with the N-hydroxysuccinimide or pentafluorophenyl ester of monoethyl (2R,3R)-trans-epoxysuccinate (6a-6b). A nucleophilic oxirane ring opening by N-hydroxysuccinimide and pentafluorophenol during the preparation of the active esters could not be observed. Subsequent saponification of the monoethyl ester 7a-7d with KOH in ethanolic solution allowed to produce the dipeptide derivatives as potassium salts (8a-8d) which were found to be stable on storage in the cold. The attempts to convert (2R,3R)-trans-epoxysuccinyl-glycyl-proline (7a) into the corresponding (2S,3S)-trans-epithiosuccinyl derivative via an oxygen sulfur exchange reaction with 3-methylbenzothiazole-2-thione failed completely as among the various products of unknown nature formed only the desulfurated fumaryl derivative could be isolated and characterized.