188109-89-9

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4S)-4-methylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester is used as a chiral building block for the synthesis of pharmaceutical compounds due to its unique stereochemistry and functional groups that can be incorporated into drug molecules.
Used in Organic Synthesis:
In the field of organic synthesis, (2S,4S)-4-methylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester serves as an intermediate for creating larger and more complex molecules, taking advantage of its reactive functional groups and chiral centers.

Upstream product

• 77-78-1 dimethyl sulfate 
• 211299-16-0 1-(tert-butyl) 2-methyl 4-(acetylthio)pyrrolidine-1,2-dicarboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 74844-91-0 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate 
• 84520-67-2 (2S,4R)-4-(methylsulfonyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butylester-2-methylester 
• 51-35-4 4R-4-hydroxyproline 
• 957475-67-1 1-tert-butyl 2-methyl (2S,4S)-4-{[(4-bromophenyl)sulfonyl]oxy}pyrrolidine-1,2-dicarboxylate 
• 1130421-81-6 C₁₀H₁₇NO₄S 
• 74-88-4 methyl iodide 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 186320-37-6 (4R)-hydroxypyrrolidine-1,(2S)-dicarboxylic acid 2-allyl ester 1-tert-butyl ester 
• 1252640-75-7 (2S,4S)-1-tert-butyl 2-methyl 4-(methylthio)pyrrolidine-1,2-dicarboxylate 

Downstream Products

• 876953-54-7 (2S,4S)-2-[(S)-1-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-4-methylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1373164-85-2 (2S,4S)-tert-butyl 2-(5-(4-bromophenyl)-1H-imidazol-2-yl)-4-(methylthio)pyrrolidine-1-carboxylate 
• 1433280-40-0 4'-{2-[(2S,4S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-4-methylsulfanyl-pyrrolidin-2-yl]-1H-imidazol-4-yl}-2-trifluoromethoxy-biphenyl-4-carboxylic acid methyl ester 
• 1433280-19-3 [(S)-2-methyl-1-((2S,4S)-4-methylsulfanyl-2-{4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-propyl]-carbamic acid methyl ester 
• 1433280-18-2 ((S)-1-{(2S,4S)-2-[4-(4-bromo-phenyl)-1H-imidazol-2-yl]-4-methylsulfanyl-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester 
• 1373164-85-2 (2S,4S)-2-[4-(4-bromo-phenyl)-1H-imidazol-2-yl]-4-methylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 1433280-21-7 4'-{2-[(2S,4S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-4-methylsulfanyl-pyrrolidin-2-yl]-1H-imidazol-4-yl}-2-trifluoromethoxy-biphenyl-4-carboxylic acid trifluoroacetic acid salt 
• 1361249-49-1 C₄₁H₅₂N₈O₆S 
• 1373165-24-2 C₃₉H₄₉N₇O₅S 
• 1373165-20-8 C₃₂H₃₈N₆O₂S 
• 1373165-02-6 C₃₈H₅₀N₆O₄SSi 
• 1373164-83-0 C₃₉H₄₈ClN₇O₅S 
• 1373165-61-7 C₄₁H₅₁ClN₈O₆S 

Relevant academic research and scientific papers

Internal Activation of Peptidyl Prolyl Thioesters in Native Chemical Ligation

Prolyl thioesters have shown significantly lower reactivities in native chemical ligation (NCL) in comparison to that of the alanyl thioester. This report describes a mild and efficient internal activation protocol of peptidyl prolyl thioesters in NCL without using any thiol-based additives, where the introduction of a 4-mercaptan substituent on the C-terminal proline significantly improves the reactivity of prolyl thioesters via the formation of a bicyclic thiolactone intermediate. The kinetic data indicate that the reaction rate is comparable to that of the reported data of alanyl thioesters, and the mechanistic studies suggest that the ligation of two peptide segments proceeds through an NCL-like pathway instead of a direct aminolysis, which ensures the chemoselectivity and compatibility of various amino acid side chains. This 4-mercaptoprolyl thioester-based protocol also allows an efficient one-pot ligation-desulfurization procedure. The utility of this method has been further demonstrated in the synthesis of a proline-rich region of Wilms tumor protein 1.

POTENT AND SELECTIVE INHIBITORS OF HEPATITIS C VIRUS

The present invention is directed to compounds, compositions and methods for treating or preventing hepatitis C virus (HCV) infection in human subjects or other animal hosts. The compounds are as also pharmaceutically acceptable, salts, prodrugs, and othe

HEPATITIS C INHIBITOR COMPOUNDS

Compounds of Formula (I) and (II) wherein R1, R2, R3, R6, A and A' are defined herein. The compounds are useful as inhibitors of the function of NS5A protein encoded by HCV for the treatment of hepatitis C viral infection.

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.