237421-54-4

Basic information

• Product Name: tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(prop-2-enyl)pyroglutamate
• Synonyms: tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(prop-2-enyl)pyroglutamate
• CAS NO: 237421-54-4
• Molecular Weight: 325.405
• Mol File: 237421-54-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(prop-2-enyl)pyroglutamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(prop-2-enyl)pyroglutamate(237421-54-4)
• EPA Substance Registry System: tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(prop-2-enyl)pyroglutamate(237421-54-4)

Safety Data

• Hazardous Substances Data: 237421-54-4(Hazardous Substances Data)

Upstream product

• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 
• 106-95-6 allyl bromide 

Downstream Products

• 87679-37-6 trandolapril 
• 237421-67-9 tert-butyl (2S,4R)-N-tert-butoxycarbonyl-4-(2-oxo-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate 
• 237421-65-7 tert-butyl (2S,4R,7RS)-4-(2-hydroxy-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate 
• 237421-66-8 tert-butyl (2S,4R)-4-(2-oxo-3-O-tert-butyldiphenylsilyloxypropyl)-pyroglutamate 

Relevant articles and documents

A Stereoselective Synthesis of the ACE Inhibitor Trandolapril

A conceptually novel and stereoselective synthesis of the enantiopure octahydroindole building block and its conversion into the ACE inhibitor trandolapril was achieved. Key steps include the α-allylation of a protected l -pyroglutamic acid derivative, a highly diastereoselective Hosomi-Sakurai reaction and a Ru-catalyzed ring-closing metathesis of a 4,5-diallylated proline. This way, the synthesis of trandolapril was efficiently achieved in 25% overall yield (12 steps).

Versatile synthesis of inhibitors of late enzymes in the bacterial pathway to lysine

Modification of our 'ring switching' reaction has allowed us to develop a versatile synthesis of potential inhibitors of the late enzymes in the bacterial pathway to lysine. The methodology is applicable to solid phase combinatorial synthesis.