5605-46-9

Basic information

• Product Name: (3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol
• Synonyms: (3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol;N-Tosylhydroxy-L-prolinol;(2S,4R)-4-Hydroxy-1-[(4-methylphenyl)sulfonyl]pyrrolidine-2-methanol;trans-(-)-4-Hydroxy-1-(p-tolylsulfonyl)pyrrolidine-2-methanol;(3R)-5-(hydroxyMethyl)-1-tosylpyrrolidin-3-ol;(2S,4R)-4-Hydro×y-1-[(4-Methylphenyl)sulfonyl]pyrrolidine-2-Methanol
• CAS NO: 5605-46-9
• Molecular Formula: C₁₂H₁₇NO₄S
• Molecular Weight: 271.33268
• Mol File: 5605-46-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 132-133℃
• Appearance: /
• Density: 1.364
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol(5605-46-9)
• EPA Substance Registry System: (3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol(5605-46-9)

Safety Data

• Hazardous Substances Data: 5605-46-9(Hazardous Substances Data)

Usage

General Description

"(3R,5S)-5-(hydroxymethyl)-1-tosylpyrrolidin-3-ol" is a chemical compound typically recognized in the field of organic chemistry. It is predicated structured upon the stereochemistry indicated by "3R,5S", translating to distinct arrangements of atoms in space. The compound features a pyrrolidin-3-ol group, which refers to a five-membered nitrogenous ring with a hydroxyl (-OH) group at the 3rd position. It carries a hydroxymethyl group (-CH2OH) at the 5th position, functioning as an important component in the manipulation of the compound’s chemical properties. Moreover, tosyl (or tosylate) is a sulfonyl group bound to a toluene ring, attached to the pyrrolidine ring by its nitrogen atom in the 1st position. As an organic molecule, it may serve various roles and functions in many chemical reactions and applications, especially in the synthesis or modification of other complex molecules.

InChI:InChI=1S/C12H17NO4S/c1-9-2-4-12(5-3-9)18(16,17)13-7-11(15)6-10(13)8-14/h2-5,10-11,14-15H,6-8H2,1H3/t10-,11+/m0/s1

Upstream product

• 618-27-9 hydroxy L-proline 
• 440678-43-3 cis-4-hydroxy-L-prolin-ethyl ester 
• 1379039-08-3 C₄₄H₅₃NO₃SSi₂ 
• 1379039-05-0 N-p-toluenesulfonyl-4(R)-amino-5-tert-butyldiphenylsilyl-1-tert-butyldiphenylsilyloxy-2(S)-pentanol 
• 909262-73-3 4-hydroxy-1-tosylpyrrolidine-2-carboxylic acid 
• 51-35-4 4R-4-hydroxyproline 
• 98-59-9 p-toluenesulfonyl chloride 
• 20275-18-7 N--trans-4-hydroxy-L-proline 

Downstream Products

• 569656-76-4 (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol 
• 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 
• 125109-57-1 (2S,4R)-1-(4-Tolylsulfonyl)-2-(chloromethyl)-4-((4-tolylsulfonyl)oxy)pyrrolidine 
• 125109-58-2 (1S,4S)-2-(4-Tolylsulfonyl)-5-methyl-2,5-diazabicyclo<2.2.1>heptane 
• 114086-15-6 (1S,4S)-2-Methyl-2,5-diazabicyclo<2.2.1>heptane Dihydrobromide 
• 141850-22-8 Hexanedioic acid mono-[(3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl] ester 
• 141850-21-7 Hept-6-enoic acid (3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl ester 
• 141850-61-5 Hexanedioic acid mono-[(3R,5S)-5-iodomethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl] ester 
• 141850-27-3 (1R,11S)-12-(Toluene-4-sulfonyl)-2,9-dioxa-12-aza-bicyclo[9.2.1]tetradecane-3,8-dione 
• 141850-28-4 (R)-5-Methylene-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol 
• 569656-63-9 (2S)(2-tert-butyldiphenylsilyloxymethyl)-4,4-diallyl-1-(toluene-4-sulfonyl)pyrrolidine 
• 569656-77-5 [5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylidene]-acetic acid ethyl ester 
• 1025889-74-0 1-bromomethyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyl)-5-aza-spiro[2.4]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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