193538-85-1

Basic information

• Product Name: D-Proline, 3-[(methylthio)methyl]-1-[(1R)-1-phenylethyl]-, phenylmethyl ester, (3S)-
• CAS NO: 193538-85-1
• Molecular Formula: C22H27NO2S
• Molecular Weight: 369.528
• Mol File: 193538-85-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: D-Proline, 3-[(methylthio)methyl]-1-[(1R)-1-phenylethyl]-, phenylmethyl ester, (3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: D-Proline, 3-[(methylthio)methyl]-1-[(1R)-1-phenylethyl]-, phenylmethyl ester, (3S)-(193538-85-1)
• EPA Substance Registry System: D-Proline, 3-[(methylthio)methyl]-1-[(1R)-1-phenylethyl]-, phenylmethyl ester, (3S)-(193538-85-1)

Safety Data

• Hazardous Substances Data: 193538-85-1(Hazardous Substances Data)

Upstream product

• 2949-92-0 methanethiosulfonic acid S-methyl ester 
• 193538-82-8 (R)-benzyl 2-(but-3-enyl(1-phenylethyl)amino)acetate 
• 177944-16-0 (R)-N-(but-3-en-1-yl)-N-(α-methylbenzyl)amine 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 

Downstream Products

• 193538-90-8 (2S,3S)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-1,2-carboxylic acid 2-benzyl ester 1-vinyl ester 
• 193538-97-5 (2S,3S)-3-Methylsulfanylmethyl-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester 
• 193538-88-4 (2S,3R)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-1,2-carboxylic acid 2-benzyl ester 1-vinyl ester 

Relevant articles and documents

Asymmetric synthesis of (2S,3S)- and (2S,3R)-3-prolinomethionines: 3-Methylsulfanylmethyl-pyrrolidine-2-carboxylic acids

The synthesis of 3-prolinomethionine can be easily achieved in a diastereoselective and enantioselective way via zinc-enolate cyclisation. After transmetallation by CuCN.2LiCl, the zinc-copper derivative was reached with S-methyl methanesulfonothioate leading in a 'one-pot' procedure, to N-(α-methylbenzyl)-3-prolinomethinine benzyl ester. The α-methylbenzyl group was transformed in vinyl-oxycarbonyl and tertiobutyl-oxycarbonyl groups successively. Reprotonation of cis Voc prolinomethionine enolate at low temperature yielded the enantiomerically pure trans diastereoisomer.