88129-44-6

Usage

Uses

Used in Pharmaceutical Industry:
Benzenesulfonamide, 4-methyl-N-[1-methyl-2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-, (S)is used as an intermediate in the synthesis of chiral annulet of 1,4,7-triazacyclononanes for the development of pharmaceutical compounds with potential therapeutic applications.

Upstream product

• 35320-23-1 (R)-2-aminopropan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 2749-11-3 (S)-Alaninol 
• 100132-60-3 (S)-2-(toluene-4-sulfonamido)propan-1-ol 
• 4816-81-3 p-tosyl-L-alanine 

Downstream Products

• 88129-50-4 [(R)-2-(Toluene-4-sulfonylamino)-propyl]-phosphonic acid diethyl ester 
• 88129-46-8 Methyl-[(R)-2-(toluene-4-sulfonylamino)-propyl]-phosphinic acid ethyl ester 
• 177971-32-3 (2R)-2-methyl-1-(p-tolylsulfonyl)aziridine 
• 119461-40-4 S-(+)-2-methyl-N-p-tosylaziridine 
• 875438-78-1 (3S)-(p-toluenesulfonyl)amino-butyronitrile 
• 875438-86-1 (3S)-3-[N-(3-methylbut-2-enyl)-N-(p-toluenesulfonyl)amino]butanal 
• 875438-81-6 N-(2-cyano-1-methyl-ethyl)-4-methyl-N-(3-methyl-but-2-enyl)-benzenesulfonamide 
• 460743-46-8 N-[(1S)-2-(benzylamino)-1-methylethyl]-4-methylbenzenesulfonamide 
• 462119-79-5 4-methyl-N-{(1S)-1-methyl-2-[((2S)-3-methyl-2-{[(4-methylphenyl)sulfonyl]amino}butyl)amino]ethyl}benzenesulfonamide 
• 462119-75-1 N-{(1S)-2-[benzyl((2S)-3-methyl-2-{[(4-methylphenyl)sulfonyl]amino}butyl)amino]-1-methylethyl}-4-methylbenzenesulfonamide 
• 462119-82-0 4-methyl-N-((1S)-1-methyl-2-{((2S)-3-methyl-2-{[(4-methylphenyl)sulfonyl]amino}butyl)[(4-methylphenyl)sulfonyl]amino}ethyl)benzenesulfonamide 
• 462119-85-3 (2S,6S)-2-isopropyl-6-methyl-1,4,7-tris[(4-methylphenyl)sulfonyl]-1,4,7-triazacyclononane 
• 34542-12-6 4-methyl-N-[(1S)-1-methyl-2-phenylethyl]benzenesulfonamide 
• 406938-17-8 N-(2-benzo[b]thiophen-3-yl-1-methyl-ethyl)-4,N-dimethyl-benzenesulfonamide 

Relevant academic research and scientific papers

Synthesis of Enantiopure PZM21: A Biased Agonist of the Mu-Opioid Receptor

PZM21 (1) was recently reported as a biased agonist of the mu-opioid receptor (MOR) with improved antinociceptive effects and reduced side effects compared with traditional opioid-based analgesics. The original synthesis of PZM21 with the desired (S,S) configuration required the separation of a diastereomeric mixture in the final step by using chiral HPLC. A concise synthesis of 1 has now been developed in the enantiomeric pure form starting with commercially available l-alanine and proceeding via a chiral aziridine as a key intermediate. The final product was obtained as the (S,S) diastereomer in seven steps in 22.5 % yield from l-alanine. This synthetic strategy could be readily applied to the development of PZM21 analogues at the thiophenyl position.

Modular One-Step Three-Component Synthesis of Tetrahydroisoquinolines Using a Catellani Strategy

Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza-Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2-alkyl- and 2-aryl-substituted aziridines to access 1,3-cis-substituted and 1,4-cis-substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.

Stereoselective synthesis of 2,4,5-trisubstituted piperidines via radical cyclization

A novel approach to 2,4,5-trisubstituted piperidines is reported, involving the 6-exo cyclization of stabilized radicals onto α,β-unsaturated esters. Only two of the four possible diastereoisomers are observed, with diastereomeric ratios ranging from 3:2

Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonyl ene and Prins cyclisations

An approach to 2,4,5-trisubstituted piperidines is reported, in which the key step is the Prins or carbonyl ene cyclisation of aldehydes of the type 1. Prins cyclisation catalysed by concentrated hydrochloric acid in CH 2Cl2 at -78 °C afforded good yields of two of the four possible diastereomeric piperidines, with the 4,5-cis product 7 predominating in a diastereomeric ratio of up to 94: 6. The diastereoselectivity of the cyclisation decreased as the 2-substituent increased in size, becoming unselective for very bulky 2-substituents. In contrast, cyclisation catalysed by MeAlCl2 in CH2Cl2 or CHCl3 at temperatures of between 20-60 °C, favoured the 4,5-trans diastereomer 8, in a diastereomeric ratio of up to 99: 1. The low-temperature cyclisations catalysed by HCl proceed under kinetic control via a mechanism involving the development of significant carbocationic character, in which the 4,5-cis cation is more stable than the 4,5-trans cation as a result of overlap with the neighbouring oxygen. The cyclisations catalysed by MeAlCl2 proceed under thermodynamic control, affording the product in which both the 4- and 5-substituents are equatorial.

Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonyl ene and Prins cyclisations

Intramolecular carbonyl ene reactions present a method for ring closure, leading to the formation of two contiguous stereocentres with an often high degree of stereocontrol. The extension of this approach to the synthesis of 2,4,5-trisubstituted piperidin

NOVEL B1 BRADYKININ RECEPTOR ANTAGONISTS

The invention encompasses novel compounds of a formula I and pharmaceutically acceptable derivatives thereof, pharmaceutical compositions and methods for treatment of diseases mediated by B1 bradykinin receptor.

The synthesis of chiral annulet 1,4,7-triazacyclononanes

Novel and flexible routes for the synthesis of chiral ring annulet 2,6-disubstituted 1,4,7-trimethyl-1,4,7-triazamacrocycles are described. Efficient macrocyclisations were realised provided that chiral analogues of N,N-bis-[2-(toluene-sulfonylamino)ethyl]-toluene-4-sulfonamide were used as the nucleophilic components. Complexes prepared, in situ, from these 2,6-disubstituted 1,4,7-trimethyl-1,4,7-triazamacrocycles and manganese(II) catalysed the asymmetric epoxidation of styrene with hydrogen peroxide.

A new convenient approach to chiral β-aryl(heteroaryl)alkylamines

Chiral β-aryl(heteroaryl)alkylamines have been prepared from N-tosyl alkylaziridines via regiospecific nucleophilic ring opening and subsequent desulfonylation in good to excellent yields. The corresponding aziridines are easily obtained from commercially available (S)-α-amino acids, so this method is the first effective route to asymmetric β-aryl(heteroaryl)alkylamines.

Synthesis of macrocyclic insect-derived alkaloids

Macrocyclic lactonic alkaloids found in the pupal secretions of two species of a coccinellid beetle (genus Epilachna) were prepared in enantiomerically pure form via an efficient synthetic route using enantiomerically pure α-amino acids as chiral-pool starting materials. Macrocycles with rings containing up to 98 atoms were synthesized in good yield using Mukaiyama's macrolactonization conditions.

C3-Symmetric tripodal tetra-amines - preparation from chiral amino alcohols via aziridines

Enantiopure N-sulfonylaziridines, conveniently obtained from readily available enantiopure amino alcohols, undergo smooth ring opening reactions using ammonia as a nucleophile to yield tripodal tetradentate C3-symmetric amines. N-alkylation and