16257-57-1

Basic information

• Product Name: METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE
• Synonyms: METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE;(2S,4R)-Methyl 4-hydro×y-1-tosylpyrrolidine-2-carbo×ylate;Methyl 4-hydroxy-1-tosylpyrrolidine-2-carboxylate;XUMMBVXGIOJOPC-PWSUYJOCSA-N
• CAS NO: 16257-57-1
• Molecular Formula: C₁₃H₁₇NO₅S
• Molecular Weight: 299.34
• Mol File: 16257-57-1.mol

Chemical Properties

• Melting Point: 97-99°C
• Boiling Point: 455.3 °C at 760 mmHg
• Flash Point: 229.1 °C
• Appearance: /
• Density: 1.373 g/cm³
• Vapor Pressure: 4.43E-09mmHg at 25°C
• Refractive Index: 1.586
• Storage Temp.: 2-8°C
• PKA: 13.88±0.40(Predicted)
• CAS DataBase Reference: METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE(16257-57-1)
• EPA Substance Registry System: METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE(16257-57-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 16257-57-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE is used as a pharmaceutical intermediate for the synthesis of various drugs, leveraging its versatile properties and reactivity to contribute to the development of new medicinal compounds.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE is employed as a potential target for research, exploring its pharmacological potential and therapeutic applications to advance the discovery of novel treatments and therapies.

InChI:InChI=1/C13H17NO5S/c1-9-3-5-11(6-4-9)20(17,18)14-8-10(15)7-12(14)13(16)19-2/h3-6,10,12,15H,7-8H2,1-2H3/t10-,12-/m1/s1

Upstream product

• 67-56-1 methanol 
• 20275-18-7 N--trans-4-hydroxy-L-proline 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 186581-53-3 diazomethane 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 16257-73-1 N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester 
• 261157-01-1 methyl N-toluenesulfonyl-O-t-butyldimethylsilyl-4-hydroxyprolinate 
• 863396-17-2 (2S)-1-(4-methylphenylsulfonyl)-2-vinylpyrrolidin-4-one 
• 863396-16-1 (2S,4R)-1-(4-methylphenylsulfonyl)-2-vinyl-4-(t-butyldimethylsilyloxy)pyrrolidine 
• 863396-18-3 (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde 
• 261157-02-2 (2S,4R)-1-(4-methylphenyl)sulfonyl-2-hydroxymethyl-4-(t-butyldimethylsilanyloxy)pyrrolidine 
• 870246-63-2 (2R)-2-(but-3-en-1-yl)-1-(4-methylphenyl)sulfonyl-2-pyrrolidin-4-one 
• 870246-70-1 3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionaldehyde 
• 870246-66-5 (2R,4R)-2-(but-3-en-1-yl)-4-(t-butyldimethylsilanyloxy)-1-(4-methylphenyl)sulfonyl-pyrrolidine 
• 870246-65-4 3-[(2R,4R)-1-(4-methylphenyl)sulfonyl-4-(t-butyldimethylsilanyloxy)pyrrolidin-2-yl]-propan-1-ol 
• 870246-68-7 (E)-(R)-2-Butyl-10-(toluene-4-sulfonyl)-10-aza-bicyclo[7.2.1]dodec-5-en-1-ol 
• 870246-69-8 3-[(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propionic acid ethyl ester 
• 870246-62-1 (R)-5-But-3-enyl-3-(1-butyl-pent-4-enyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol 
• 2650-35-3 (–)-(6S,10aR,10bS)-norsecurinine 

Relevant articles and documents

Diastereoselective Diboration of Cyclic Alkenes: Application to the Synthesis of Aristeromycin

The Pt-catalyzed diboration of cyclic alkenes is extended to unsaturated heterocycles and bicyclic compounds and can be accomplished in a diastereoselective fashion. The optimal procedures, substrate scope, and diastereoselectivity were investigated, and examples employing both homogeneous and heterogeneous catalysis were examined. Lastly, application to the construction of the nucleoside analog (±)-aristeromycin was conducted.

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A series of novel α-sulfonyl γ-(glycinyl-amino)proline peptidomimetic derivatives were designed, synthesized and assayed for their activities against matrix metalloproteinase-2 (MMP-2), aminopeptidase N (APN)/CD13 and HDACs. The results indicated that all the compounds exhibited highly selective inhibition against MMP-2 as compared with APN and HDACs. The antiproliferative activities of some compounds against SKOV3, HL60 and A549 cells were also investigated. Comparing with the control LY52, compound 12u, with excellent activity both in the enzymatic inhibition assay and cell-based assay, could be used as lead compound for the further development of MMP inhibitors.

Design, synthesis and evaluation of novel sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors

A series of novel sulfonyl pyrrolidine derivatives were designed, synthesized and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. Compounds 6a-d were more potent MMP-2 inhibitors than the positive control LY52. The structure-activity relationships were also briefly discussed.

Synthesis of new sulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors

A series of new sulfonyl pyrrolidine derivatives was designed, synthesized, and assayed for their inhibitory activities on matrix metalloproteinase 2 (MMP-2) and aminopeptidase N (AP-N). The results showed that these pyrrolidine derivatives exhibited highly selective inhibition against MMP-2 as compared with AP-N. The compounds 4c, 4j, 5a, and 5b were equally or more potent MMP-2 inhibitors than the positive control LY52. The FlexX docking was done to explain the reason for the different potency between MMP-2 and AP-N. Structure-activity relationships were also briefly discussed.

Formal synthesis of epibatidine

A straightforward formal synthesis of epibatidine has been established starting from trans-(2S,4R)-4-hydroxyproline.

Synthesis of streptorubin B core

A straightforward synthesis of streptorubin B core structure has been established starting from trans-4-hydroxyproline. The core structure of streptorubin B is constructed in an intramolecular ring-closing metathesis as the key step.

Trans-4-aminoproline, a phytotoxic metabolite with herbicidal activity produced by Ascochyta caulina

A phytotoxic metabolite, characterized through NMR techniques and synthetic methods as trans-4-aminoproline, was isolated from the culture filtrates of Ascochyta caulina, a promising mycoherbicide for biological control of Chenopodium album. The metabolite, which shows interesting phytotoxic properties, together with ascaulitoxin (recently characterized as N2-β-D-glucoside of the unusual bis-amino acid 2,4,7-triamino-5- hydroxyoctandioc acid) and another unidentified compound, compose an active fraction of A. caulina culture filtrates with promising herbicidal properties. When assayed on leaves of host and non host dicots, including wild and cultivated plants, the trans-4-aminoproline showed a wide range of toxicity, with leaves of C. album being the most sensitive. Other interesting aspects were its inefficacy on several monocots, both cultivated and wild, and its lack of antifungal, antibiotic and zootoxic activities. This is the first report on trans-4-aminoproline as naturally occurring compound and phytotoxic metabolite produced by A. caulina. (C) 2000 Elsevier Science Ltd.

Synthesis and biological properties of a new series of 5-substituted- pyrimidine-L-nucleoside analogues

trans-4-hydroxy-L-proline (5) has been elaborated into a new series of pyrrolidine-L-nucleoside analogues incorporating non-standard 5-substituted- pyrimidine nucleobases, via the azidopyrrolidines 12 and 13. Those analogues employing an acyl protecting group on the primary hydroxyl functionality underwent radical bromination of the ethyl side chain of the pyrimidine ring, to provide E-5-(2-bromovinyl)uracil-pyrrolidine-L-nucleosides 23-26. Of the compounds assessed for potential antiviral activity only 5-ethyluracil- (benzoyloxymethyl)pyrrolidine 20 was found to be a specific inhibitor of vaccinia virus.

Synthesis of (2R,3R,4S)-2-hydroxymethylpyrrolidine-3,4-diol from (2S)-3,4-dehydroproline derivatives

(2R,3R,4S)-2-Hydroxymethylpyrrolidine-3,4-diol (1,4-dideoxy-1,4-imino-D-ribitol) was synthesized in five steps from N-protected (2S)-3,4-dehydroproline methyl esters.The stereoselective reaction of osmium tetraoxide with dehydroproline derivatives gave hi