366498-39-7

Basic information

• Product Name: (3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(2-methyl-1-propenyl)-L-proline methyl ester
• Synonyms: (3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(2-methyl-1-propenyl)-L-proline methyl ester
• CAS NO: 366498-39-7
• Molecular Weight: 359.466
• Mol File: 366498-39-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(2-methyl-1-propenyl)-L-proline methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(2-methyl-1-propenyl)-L-proline methyl ester(366498-39-7)
• EPA Substance Registry System: (3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(2-methyl-1-propenyl)-L-proline methyl ester(366498-39-7)

Safety Data

• Hazardous Substances Data: 366498-39-7(Hazardous Substances Data)

Upstream product

• 366498-32-0 (3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester 
• 366498-31-9 methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate 
• 29917-94-0 2-methylprop-1-enyllithium 
• 366498-36-4 (3S)-N-tert-butyloxycarbonyl-5-methoxy-3-phenyl-L-proline methyl ester 

Downstream Products

• 366498-37-5 (3S,5S)-N-(Cbz-Phe)-3-phenyl-5-(2-methyl-1-propenyl)-L-proline methyl ester 

Relevant articles and documents

Building constrained peptidomimetics: A convenient approach to 3-phenyl-5-vinyl substituted proline derivatives

An approach to the synthesis of 3-phenyl-5-vinyl substituted prolines starting from readily available 2,3-disubstituted pentenoic acid derivatives is reported. The route converts the pentenoic acid derived starting materials into cyclic N-acyliminium ion precursors with the use of a hydroboration-Swern oxidation sequence. This overall transformation worked best when the initial alkylborane product was treated sequentially with excess MCPBA and then acetone prior to the Swern oxidation. In this way, a 70% yield of the desired N-acyliminium ion precursor could be obtained. Once in hand, the cyclic N-acyliminium ion precursor was used to make the desired 3-phenyl-5-vinyl substituted prolines.