118329-82-1

Basic information

• Product Name: (3R,5S)-5-(HYDROXYMETHYL)-1-TOSYLPYRROLIDIN-3-YL 4-METHYLBENZENESULFONATE
• Synonyms: (3R,5S)-5-(HYDROXYMETHYL)-1-TOSYLPYRROLIDIN-3-YL 4-METHYLBENZENESULFONATE
• CAS NO: 118329-82-1
• Molecular Formula: C₁₉H₂₃NO₆S₂
• Molecular Weight: 425.52
• Mol File: 118329-82-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3R,5S)-5-(HYDROXYMETHYL)-1-TOSYLPYRROLIDIN-3-YL 4-METHYLBENZENESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5S)-5-(HYDROXYMETHYL)-1-TOSYLPYRROLIDIN-3-YL 4-METHYLBENZENESULFONATE(118329-82-1)
• EPA Substance Registry System: (3R,5S)-5-(HYDROXYMETHYL)-1-TOSYLPYRROLIDIN-3-YL 4-METHYLBENZENESULFONATE(118329-82-1)

Safety Data

• Hazardous Substances Data: 118329-82-1(Hazardous Substances Data)

Usage

Description

(3R,5S)-5-(HydroxyMethyl)-1-TosylPyrrolidin-3-yl 4-MethylBenzenesulfonate is a complex organic chemical compound with the molecular formula C17H21NO4S. It is a tosylate derivative of a pyrrolidine compound, featuring a hydroxymethyl group attached to the pyrrolidine ring. The tosyl group, which contains a sulfonate ester, serves as a leaving group in organic synthesis, while the 4-methylbenzenesulfonate group acts as a protecting group in organic chemistry. (3R,5S)-5-(HYDROXYMETHYL)-1-TOSYLPYRROLIDIN-3-YL 4-METHYLBENZENESULFONATE's unique structural features and reactivity may contribute to its potential applications in organic synthesis, medicinal chemistry, and pharmaceutical research.

Uses

Used in Organic Synthesis:
(3R,5S)-5-(HydroxyMethyl)-1-TosylPyrrolidin-3-yl 4-MethylBenzenesulfonate is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its tosyl group serves as a leaving group, facilitating reactions such as nucleophilic substitutions and eliminations, while the 4-methylbenzenesulfonate group provides stability and protection during the synthesis process.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (3R,5S)-5-(HydroxyMethyl)-1-TosylPyrrolidin-3-yl 4-MethylBenzenesulfonate may be utilized as a building block for the development of novel pharmaceutical compounds. Its unique structure and reactivity can be exploited to create new molecules with potential therapeutic properties, contributing to the discovery of new drugs and treatments for various diseases.
Used in Pharmaceutical Research:
(3R,5S)-5-(HydroxyMethyl)-1-TosylPyrrolidin-3-yl 4-MethylBenzenesulfonate is also used in pharmaceutical research for the investigation of its potential biological activities and therapeutic applications. Researchers may explore its interactions with biological targets, such as enzymes, receptors, or other proteins, to understand its potential as a lead compound in drug discovery and development.

Upstream product

• 16257-73-1 N,O-ditosyl-trans-4-hydroxy-L-proline methyl ester 
• 118329-81-0 (2S,4R)-2-ethoxycarbonyl-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine 
• 51-35-4 4R-4-hydroxyproline 
• 61478-25-9 (2S,4R)-4-hydroxypyrrolidine-2-carboxylic acid ethyl ester 
• 40216-83-9 L-4-hydroxyproline methyl ester hydrochloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 5260-29-7 N,O-ditosylhydroxy-L-proline 

Downstream Products

• 22324-34-1 (2S,4R)-N-Tosyl-4-tosyloxy-O-benzoylprolinol 
• 216692-09-0 Toluene-4-sulfonic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl ester 
• 863392-58-9 (2S,4R)-2-(carbamoyloxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine 
• 863392-52-3 (S)-2-carbamoyloxymethyl-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole 
• 863392-54-5 (2S,3S,4R)-2-hydroxymethyl-3,4-(oxazol-2-one)-1-(toluene-4-sulfonyl)pyrrolidine 
• 863392-59-0 (2S,4S)-2-(carbamoyloxymethyl)-4-phenylselanyl-1-(toluene-4-sulfonyl)pyrrolidine 
• 216860-64-9 Benzoic acid (2S,4S)-4-amino-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester 
• 216692-63-6 5-Ethyl-1-[(3S,5S)-5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-1H-pyrimidine-2,4-dione 
• 22324-35-2 Benzoic acid (2S,4S)-4-azido-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester 
• 216692-78-3 Acetic acid (2S,4S)-4-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester 
• 216692-83-0 Acetic acid (2S,4S)-4-[5-((E)-2-bromo-vinyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester 
• 216692-27-2 (3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ylamine 
• 216692-57-8 Benzoic acid (2S,4S)-4-(5-ethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester 
• 216692-17-0 (2S,4S)-4-Azido-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidine 

Relevant articles and documents

Chemoenzymatic synthesis and cannabinoid activity of a new diazabicyclic amide of phenylacetylricinoleic acid

Endocannabinoids (eCBs) are endogenous neuromodulators of synaptic transmission. Their dysfunction may cause debilitating disorders of diverse clinical manifestation. For example, drug addiction, lack of sex desire, eating disorders, such as anorexia or bulimia and dyssomnias. eCBs also participate in the regulation of core temperature and pain perception. In this context, it is important to recognize the utility of cannabinoid receptor 1 (CB1R) agonists, natural as Δ9-tetrahydrocannabinol (THC) or synthetic as Nabilone as useful drugs to alleviate this kind of patients' suffering. Therefore, we have developed a new drug, (R,Z)-18-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-18-oxooct adec-9-en-7-yl phenylacetate (PhAR-DBH-Me), that appears to bind and activate the CB1R. This diazabicyclic amide was synthesized from phenylacetylricinoleic acid and (1S,4S)-2,5-diazabicyclo[2.2.1]heptane. To test its cannabinergic properties we evaluated its effects on core temperature, pain perception, and the sleep-waking cycle of rats. Results indicate that 20 and 40 mg/kg of PhAR-DBH-Me readily reduced core temperature and increased pain perception threshold. In addition, 20 mg/kg increased REM sleep in otherwise normal rats. All these effects were prevented or attenuated by AM251, a CB1R antagonist. Place preference conditioning studies indicated that this molecule does not produce rewarding effects. These results strongly support that PhAR-DBH-Me possesses cannabinoid activity without the reinforcement effects.

The first asymmetric synthesis of (2S,3S,4R)-3-amino-2-hydroxymethyl-4- hydroxypyrrolidine

The novel (2S,3S,4R)-3-amino-2-hydroxymethyl-4-hydroxypyrrolidine 5 has been produced in an efficient synthesis from trans-4-hydroxy-l-proline 8. The key step involves a tethered aminohydroxylation of the alkene 7 to introduce regio- and stereoselectively