876953-58-1

Basic information

• Product Name: 1,2-Pyrrolidinedicarboxylic acid, 4-(methylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4R)-
• Synonyms: (2S,4R)-4-Methylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
• CAS NO: 876953-58-1
• Molecular Formula: C11H19NO4S
• Molecular Weight: 261.33800
• Mol File: 876953-58-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-(methylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Pyrrolidinedicarboxylic acid, 4-(methylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4R)-(876953-58-1)
• EPA Substance Registry System: 1,2-Pyrrolidinedicarboxylic acid, 4-(methylthio)-, 1-(1,1-dimethylethyl) ester, (2S,4R)-(876953-58-1)

Safety Data

• Hazardous Substances Data: 876953-58-1(Hazardous Substances Data)

Usage

Functional groups

Ester, carboxylic acid, and thiol

Chiral centers

Two (C2 and C4)

Possible stereoisomers

Four (2R,4R), (2R,4S), (2S,4R), and (2S,4S)

Specific stereoisomer

(2S,4R)-

Structure

Ester derivative of 1,2-pyrrolidinedicarboxylic acid with a methylthio group and a 1,1-dimethylethyl group

Applications

Intermediate or building block in the synthesis of pharmaceuticals and other organic compounds

Physical state

Likely a solid at room temperature (based on molecular size and complexity)

Solubility

Likely soluble in organic solvents such as ethanol, methanol, or acetone, and may have limited solubility in water

Stability

Stable under normal conditions, but sensitive to heat, light, and moisture (as with most organic compounds)

Upstream product

• 121147-93-1 (2S,4S)-2-methyl N-Boc-4-((methylsulfonyl)oxy)pyrrolidine-2-carboxylate 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 74844-91-0 (2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 188111-18-4 1-(tert-butyl) 2-methyl (2S,4R)-4-(acetylthio)pyrrolidine-1,2-dicarboxylate 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 876953-56-9 (2S,4R)-2-[(S)-1-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-4-methylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Chemotactic peptides: fMLF-OMe analogues incorporating proline-methionine chimeras as N-terminal residue

The new fMLF analogues 1-4, incorporating chimeric S-proline-methionine residues (namely the homochiral cis-4(S)-methylthio-(S)-proline (10) and the heterochiral trans-4(R)-methylthio-(S)-proline) (17) in place of the native S-methionine, have been prepared; their solution conformation and activity as agonists or antagonists of formylpeptide receptors have been studied. In addition to peptides 1-4, which maintain the Met γ-thiomethyl-ether function, the analogues Boc-PLF-OMe (18) and For-PLF-OMe (19) devoid, as compared with 1-4, of position 1 side chain, have been synthesized and their activity examined.