760968-59-0

Basic information

• Product Name: (2R)-but-3-enyl-(5R)-2-(1-methylsiletan-1-ylethynyl)pyrrolidine-1-carboxylic acid benzyl ester
• Synonyms: (2R)-but-3-enyl-(5R)-2-(1-methylsiletan-1-ylethynyl)pyrrolidine-1-carboxylic acid benzyl ester
• CAS NO: 760968-59-0
• Molecular Weight: 367.563
• Mol File: 760968-59-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R)-but-3-enyl-(5R)-2-(1-methylsiletan-1-ylethynyl)pyrrolidine-1-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-but-3-enyl-(5R)-2-(1-methylsiletan-1-ylethynyl)pyrrolidine-1-carboxylic acid benzyl ester(760968-59-0)
• EPA Substance Registry System: (2R)-but-3-enyl-(5R)-2-(1-methylsiletan-1-ylethynyl)pyrrolidine-1-carboxylic acid benzyl ester(760968-59-0)

Safety Data

• Hazardous Substances Data: 760968-59-0(Hazardous Substances Data)

Upstream product

• 690211-35-9 (2R)-benzyloxycarbonylamino-5-oxonon-8-enoic acid methyl ester 
• 690211-34-8 1-benzyl 2-methyl (R)-5-oxopyrrolidine-1,2-dicarboxylate 
• 501-53-1 benzyl chloroformate 
• 64700-65-8 methyl (2R)-pyroglutamate 
• 2351-34-0 1-chloro-1-methylsiletane 
• 690211-37-1 (2R,5R)-5-but-3-enyl-2-ethynylpyrrolidine-1-carboxylic acid 1-benzyl ester 

Downstream Products

• 690211-40-6 (+)-(1R)-2-(1,2-dihydroxy-1-methylethyl)-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene 
• 690211-39-3 (+)-(1R)-2-isopropenyl-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene 
• 690211-38-2 (2R)-but-3-enyl-(5R)-prop-1-ynylpyrrolidine-1-carboxylic acid 1-benzyl ester 
• 120692-41-3 (+)-(1R)-2-acetyl-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene 
• 64285-06-9 anatoxin-a 
• 690211-37-1 (2R,5R)-5-but-3-enyl-2-ethynylpyrrolidine-1-carboxylic acid 1-benzyl ester 

Relevant articles and documents

Enantioselective synthesis of (+)-anatoxin-a via enyne metathesis

A concise synthesis of the potent nAChR agonist (+)-anatoxin-a (1) has been completed by a series of nine chemical operations and in 27% overall yield from commercially available D-methyl pyroglutamate (12). The strategy featured the application of a new protocol for the diastereoselective synthesis of cis-2,5-disubstituted pyrrolidines bearing unsaturated side chains and an intramolecular enyne metathesis to provide the bridged bicyclic framework of 1. Thus, D-methyl pyroglutamate (12) was converted in five steps to 32, which underwent facile enyne metathesis to deliver the bicyclic diene 33. Selective oxidative cleavage of the less substituted carbon-carbon double bond in 33 followed by deprotection furnished (+)-anatoxin-a (1).