116143-08-9

Basic information

• Product Name: (2R,4S)-2-(Hydroxymethyl)-4-hydroxy-1-(4-tolylsulfonyl)pyrrolidine
• Synonyms: (2R,4S)-2-(Hydroxymethyl)-4-hydroxy-1-(4-tolylsulfonyl)pyrrolidine
• CAS NO: 116143-08-9
• Molecular Weight: 271.337
• Mol File: 116143-08-9.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: (2R,4S)-2-(Hydroxymethyl)-4-hydroxy-1-(4-tolylsulfonyl)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,4S)-2-(Hydroxymethyl)-4-hydroxy-1-(4-tolylsulfonyl)pyrrolidine(116143-08-9)
• EPA Substance Registry System: (2R,4S)-2-(Hydroxymethyl)-4-hydroxy-1-(4-tolylsulfonyl)pyrrolidine(116143-08-9)

Safety Data

• Hazardous Substances Data: 116143-08-9(Hazardous Substances Data)

Upstream product

• 77449-94-6 (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid hydrochloride 
• 114676-59-4 (2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride 
• 142928-26-5 (2R,4S)-1-(4-tolylsulfonyl)-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-<(3,5-dimethyl-1H-pyrazol-1-yl)-carbonyl>pyrrolidine 
• 1075183-51-5 N-tosyl hydroxyproline methyl ester 
• 141621-09-2 (2R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid 
• 141621-10-5 (2R,4S)-1-(4-tolylsulfonyl)-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-formylpyrrolidine 
• 1076206-58-0 (4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[(4-methylphenyl)sulfonyl]-D-proline methyl ester 
• 1379039-10-7 C₄₄H₅₃NO₃SSi₂ 
• 1379039-06-1 N-p-toluenesulfonyl-4(R)-amino-5-tert-butyldiphenylsilyl-1-tert-butyldiphenylsilyloxy-2(R)-pentanol 
• 1076206-60-4 (2R,4S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[(4-methylphenyl)sulfonyl]-2-pyrrolidinemethanol 
• 2584-71-6 cis-hydroxy-D-proline 
• 132666-67-2 (2S,4R)-ethyl 4-hydroxypyrrolidine-2-carboxylate 
• 51-35-4 4R-4-hydroxyproline 
• 116143-05-6 allo-1-(4-tolylsulfonyl)-4-<<(4-methylphenyl)sulfonyl>oxy>-D-proline ethyl ester 

Downstream Products

• 906065-75-6 toluene-4-sulfonic acid 5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester 
• 135042-28-3 cis-4-(6-amino-9H-purin-9-yl)-D-prolinol 
• 125109-57-1 (2S,4R)-1-(4-Tolylsulfonyl)-2-(chloromethyl)-4-((4-tolylsulfonyl)oxy)pyrrolidine 
• 5234-75-3 (2S,4R)-1-(4-tolylsulfonyl)-4-<(4-tolylsulfonyl)oxy>-2-<<(4-tolylsulfonyl)oxy>methyl>pyrrolidine 
• 1076206-66-0 (1R,4R)-2-[(2,3,5-trifluorophenyl)methyl]-2,5-diazabicyclo[2.2.1]heptane 
• 1076206-64-8 (1R,4R)-2-[(4-methylphenyl)sulfonyl]-5-[(2,3,5-trifluorophenyl)methyl]-2,5-diazabicyclo[2.2.1]heptane 
• 5234-72-0 (1S,4S)-5-Benzyl-2-tosyl-2,5-diazabicyclo<2.2.1>heptane 
• 127641-07-0 (1S,4S)-N-Benzyl-2,5-diazabicyclo-[2.2.1]heptane 
• 116143-32-9 7-<(1R,4R)-2,5-diazabicyclo<2.2.1>heptan-2-yl>-1-(1,1-dimethylethyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid 
• 116258-17-4 (1R,4R)-5-phenylmethyl-2,5-diazabicyclo[2.2.1] heptane dihydrobromide 
• 118354-72-6 (1R,4R)-2-(4-tolylsulfonyl)-5-(phenylmethyl)-2,5-diazabicyclo<2.2.1>heptane 
• 114086-15-6 (1S,4S)-2-Methyl-2,5-diazabicyclo<2.2.1>heptane Dihydrobromide 
• 114086-15-6 (1R,4R)-2-Methyl-2,5-diazabicyclo<2.2.1>heptane dihydrobromide 
• 125224-63-7 (1R,4R)-2-(4-Tolylsulfonyl)-5-methyl-2,5-diazabicyclo<2.2.1>heptane 

Relevant articles and documents

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A smooth rearrangement of N-p-toluenesulfonyl 2-tert- butyldiphenylsilylmethyl-substituted azetidines into N-p-toluenesulfonyl 3-tert-butyldiphenylsilyl-substituted pyrrolidines

The rearrangement of N-p-toluenesulfonyl 2-tert-butyldiphenylsilylmethyl- substituted azetidines into 3-tert-butyldiphenylsilyl-substituted pyrrolidines under Lewis acid conditions in dichloromethane involves 1,2-migration of silicon through a siliranium ion. The formation of siliranium ion was discovered not to be in concert with σC-N cleavage from stereochemical analysis of the pyrrolidine products formed from 3- and 4-substituted-2-tert- butyldiphenylsilylmethyl azetidines and also from the optical rotation data and chiral HPLC analysis of the pyrrolidine product formed from N-p-toluenesulfonyl 2(R)-tert-butyldiphenylsilylmethyl azetidine. The formation of sterically less hindered siliranium ion is followed by its SN2 opening by the internal nitrogen nucleophile. Oxidative cleavage of σC-Si bond leads to the formation of 3-hydroxypyrrolidines.

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