212612-57-2

Basic information

• Product Name: methyl (2S,3R)-N-(tert-butoxycarbonyl)-β-phenylprolinate
• Synonyms: methyl (2S,3R)-N-(tert-butoxycarbonyl)-β-phenylprolinate
• CAS NO: 212612-57-2
• Molecular Weight: 305.374
• Mol File: 212612-57-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl (2S,3R)-N-(tert-butoxycarbonyl)-β-phenylprolinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S,3R)-N-(tert-butoxycarbonyl)-β-phenylprolinate(212612-57-2)
• EPA Substance Registry System: methyl (2S,3R)-N-(tert-butoxycarbonyl)-β-phenylprolinate(212612-57-2)

Safety Data

• Hazardous Substances Data: 212612-57-2(Hazardous Substances Data)

Upstream product

• 1101927-70-1 methyl (2S,3R)-N-tert-butoxycarbonyl-3-phenylpyroglutamate 
• 51212-36-3 1-acetyl-3-phenyl-pyrrolidine-2,2-dicarboxylic acid diethyl ester 
• 3005-63-8 1-acetyl-5-hydroxy-3-phenyl-pyrrolidine-2,2-dicarboxylic acid diethyl ester 
• 210420-48-7 (2RS,3SR)-N-(tert-butoxycarbonyl)-β-phenylproline 
• 143979-44-6 1-(tert-butoxycarbonyl)-3-phenylproline 
• 1426559-89-8 C₁₁H₁₃NO₂*ClH 
• 24424-99-5 di-tert-butyl dicarbonate 
• 212612-50-5 trans-3-phenyl-L-proline methyl ester 

Downstream Products

• 118758-48-8 (2S,3R)-3-phenyl-pyrrolidine-2-carboxylic acid 
• 123724-21-0 (2S,3R)-1-(tert-butoxycarbonyl)-3-phenylpyrrolidine-2-carboxylic acid 
• 270257-64-2 (3R,5R)-N-tert-butyloxycarbonyl-3-phenyl-5-(2'-o-nitrophenylseleno)ethyl-L-proline methyl ester 
• 270257-63-1 (3R,5R)-N-tert-butyloxycarbonyl-3-phenyl-5-(2'-hydroxyethyl)-L-proline methyl ester 
• 270257-59-5 (3R,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-allyl-L-proline methyl ester 
• 270257-60-8 (3R,5R)-N-tert-butyloxycarbonyl-3-phenyl-5-vinyl-L-proline methyl ester 
• 212612-52-7 (3R,5S)-N-benzyloxycarbonyl-L-phenylalanine-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester 
• 270257-65-3 (3S,6S,8R,9S)-N-benzyloxycarbonyl-1,4-diaza-3-benzyl-9-carbomethoxy-5-hydroxy-8-phenyl-2-oxobicylo[4.3.0]nonane 
• 212612-62-9 (3S,6S,8R,9S)-N-tert-butyloxycarbonyl-1,4-diaza-3-benzyl-9-carbomethoxy-8-phenyl-2-oxobicylo[4.3.0]nonane 
• 212612-53-8 (3S,6S,8R,9S)-1,4-diaza-3-benzyl-9-carbomethoxy-8-phenyl-2-oxobicylo[4.3.0]nonane 
• 212612-58-3 (3R,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester 
• 212612-60-7 (2S,3R,5S)-3-Phenyl-5-((E)-propenyl)-pyrrolidine-2-carboxylic acid methyl ester 
• 212612-51-6 (3R)-N-tert-butyloxycarbonyl-5-methoxy-3-phenyl-L-proline methyl ester 

Relevant articles and documents

Access to enantiomerically pure cis- and trans-β-phenylproline by high-performance liquid chromatography resolution

The preparation of all four stereoisomers of the proline analog that bears a phenyl group attached to the β carbon either cis or trans to the carboxylic acid (cis- and trans-β-phenylproline, respectively) has been addressed. The methodology developed allows access to multigram quantities of the target amino acids in enantiomerically pure form and suitably protected for use in peptide synthesis. Racemic precursors of cis-β-phenylproline and trans-β-phenylproline were prepared from easily available starting materials and subjected to high-performance liquid chromatography enantioseparation. Semipreparative columns (250 × 20 mm) containing chiral stationary phases based on amylose (Chiralpak IA) (Daicel-Chiral Technologies Europe, Illkirch, France) or cellulose (Chiralpak IC) were used respectively for the resolution of the cis- and trans-β-phenylproline precursors. Chirality, 24:1082-1091, 2012. 2012 Wiley Periodicals, Inc. Copyright

Conformationally constrained substance P analogues: The total synthesis of a constrained peptidomimetic for the Phe7-Phe8 region

A lactam-based peptidomimetic for the Phe7-Phe8 region of substance P has been synthesized. The synthesis used an anodic amide oxidation to selectively functionalize the C5-position of a 3-pheylproline derivative. The resulting proline derivative was coupled to a Cbz-protected phenylalanine, and an intramolecular reductive amination strategy used to convert the coupled material into a bicyclic piperazinone ring skeleton. The net result was a dipeptide building block that imbedded one of two proposed receptor bound conformations for the Phe7-Phe8 region of substance P into a bicyclic ring skeleton. The building block was then converted into a constrained substance P analogue with the use of solid-phase peptide synthesis. A similar intramolecular reductive amination strategy was used to synthesize a substance P analogue having only Phe7 constrained, and the original 3-phenylproline was converted into a substance P analogue having only Phe8 constrained. All of the analogues were examined for their ability to displace substance P from its NK-1 receptor.