177971-32-3

Usage

Uses

Used in Pharmaceutical Industry:
Aziridines, including Aziridine, 2-methyl-1-[(4-methylphenyl)sulfonyl]-, (2R)-, are used as key intermediates in the synthesis of various pharmaceutical compounds. The chiral nature of this specific compound makes it particularly valuable for the development of enantiomerically pure drugs, which can have significant advantages in terms of efficacy and reduced side effects.
Used in Organic Synthesis:
Azirididine, 2-methyl-1-[(4-methylphenyl)sulfonyl]-, (2R)is used as a building block in the synthesis of complex organic molecules. Its unique structure allows for a variety of chemical reactions, such as ring-opening reactions, which can be used to construct a wide range of target molecules.
Used in the Synthesis of Tetrahydropyridines:
Azirididine, 2-methyl-1-[(4-methylphenyl)sulfonyl]-, (2R)is used as a starting material for the synthesis of tetrahydropyridines, which are important compounds in the pharmaceutical industry due to their diverse biological activities.
Used in the Synthesis of Morpholines:
This chiral aziridne is also used in the synthesis of morpholines, a class of compounds with various applications, including as pharmaceuticals, agrochemicals, and synthetic intermediates.
Used in the Synthesis of Chiral βand γ-Amino Ethers:
Aziridine, 2-methyl-1-[(4-methylphenyl)sulfonyl]-, (2R)is utilized in the preparation of chiral βand γ-amino ethers, which are valuable building blocks in the synthesis of biologically active molecules and natural products.
Used in the Synthesis of (ent)-Korupensamine D:
This specific aziridne is used in the synthesis of (ent)-Korupensamine D, a natural product with antimalarial properties. The development of new synthetic routes to such bioactive natural products can lead to the discovery of more effective treatments for various diseases.

Upstream product

• 88129-44-6 Toluene-4-sulfonic acid (R)-2-(toluene-4-sulfonylamino)-propyl ester 
• 35320-23-1 (R)-2-aminopropan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 786709-32-8 (R)-N-(1-hydroxypropan-2-yl)-4-methylbenzenesulfonamide 

Downstream Products

• 177971-33-4 (-)-(R)-N-2-(3,5-dimethoxyphenyl)-1-methylethyl (4-methylphenyl)sulfonamide 
• 362495-82-7 [2S,4R,1'S,2'S]-(-)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide 
• 1180678-19-6 2,2,5-trimethyl-3-[(4-methylbenzene)sulfonyl]-1,3-oxazolidine 
• 1244040-48-9 C₂₆H₄₀N₄O₄S₂ 
• 1265595-99-0 C₁₈H₂₅NO₃S₃ 
• 1372542-04-5 (R)-N-(1-Methoxypropan-2-yl)-4-methylbenzenesulfonamide 
• 1361969-54-1 (R)-4-methyl-N-(5-(trimethylsilyl)pent-4-yn-2-yl)benzenesulfonamide 
• 1361969-75-6 4-methyl-N-((S)-1-(pentyloxy)allyl)-N-((R)-5-(trimethylsilyl)pent-4-yn-2-yl)benzenesulfonamide 
• 1361969-82-5 4-methyl-N-((R)-1-(pentyloxy)allyl)-N-((R)-5-(trimethylsilyl)pent-4-yn-2-yl)benzenesulfonamide 
• 1265595-79-6 C₂₁H₂₉NO₄S₃ 
• 1265595-98-9 C₁₈H₂₅NO₃S₃ 
• 1265595-87-6 C₁₈H₂₇NO₃S₃ 
• 1265595-88-7 C₁₈H₂₇NO₃S₃ 

Relevant academic research and scientific papers

Achieving regio- and stereo-control in the fluorination of aziridines under acidic conditions

We developed an efficient fluorination protocol that converts easily accessible aziridines into β-fluoroamines, which are important motifs in biologically active molecules. In contrast with traditional fluorination approaches, DMPU-HF has shown both highe

A Modular Synthesis of Multidentate S-, N- and O-Containing Meta- and Paracyclophanes

The development of a modular approach to macrocycle assembly has enabled the synthesis of a library of pyridine-based macrocycles possessing multiple donor sites where chirality was readily introduced from (R)- or (S)-alanine, a representative amino acid. The facile, regioselective, nucleophilic ring opening of aziridines by dithiols enabled the synthesis of thioether-based linkers which on subsequent alkylation provided access to optically pure macrocycles. A modular approach to macrocyclic assembly has enabled the synthesis of a library of macrocycles possessing multiple donor sites where chirality was readily introduced from (S)-alanine. Key to this approach was the facile, regioselective, nucleophilic ring opening of aziridines by dithiols followed by macrocylisation under conditions of high dilution.

Stereodefined N,O-acetals: Pd-catalyzed synthesis from homopropargylic amines and utility in the flexible synthesis of 2,6-substituted piperidines

We developed a conceptually new synthetic strategy which exploits the stereochemical information of labile acyclic N,O-acetals. The key to this strategy, chemo- and stereoselective synthesis of N,O-acetals, was achieved by the Pd-catalyzed addition of sulfonyl-protected homopropargylic amines to alkoxyallene. The N,O-acetals generated in this way were combined with Au-catalyzed cycloisomerization to give an access to 2,6-disubstituted piperidines with stereochemical flexibility.

A highly diastereo-and enantioselective copper(I)-catalyzed henry reaction using a bis(sulfonamide)-diamine ligand

A series of bis(sulfonamide)-diamine (BSDA) ligands were synthesized from commercially available chiral α-amino alcohols and diamines. The chiral BSDA ligand 3a, coordinated with Cu(I), catalyzes the enantioselective Henry reaction with excellent enantios

A highly effective bis(Sulfonamide)-diamine ligand: A unique chiral skeleton for the enantioselective Cu-catalyzed Henry reaction

(Figure Presented) A skeleton in the closet! As a unique chiral skeleton, the newly developed bis(sulfonamide)-diamine, which contains both diamine and bis(sulfonamide) moieties, was a highly effective ligand for the asymmetric Cu(OAc)2-catalyz

Sc(OTf)3-catalyzed condensation of 2-alkyl-N-tosylaziridine with aldehydes or ketones: An efficient synthesis of 5-alkyl-1,3-oxazolidines

Sc(OTf)3 effectively catalyzes the condensation of 2-alkyl-N-tosylaziridine with a wide variety of aldehydes and ketones, producing 5-alkyl-1,3-oxazolidines in good yields and excellent regioselectivity at catalyst loadings as low as 1 mol%.

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.

Absolute configuration of the polyazamacrolides, macrocyclic polyamines produced by a ladybird beetle

The absolute configuration of the polyazamacrolides, oligomeric macrocycles from the pupal defensive secretion of Epilachna borealis, was determined by comparison of derivatives of the natural material with enantiomerically pure synthetic samples. Samples of a mixture of three (ω- 1)-(2-hydroxy-ethylamino)alkanoic acids and of the corresponding aza-lactones were synthesized from (R)-alaninol. Gas chromatographic comparison of MTPA- amides of the synthetic aza-lactones with the MTPA-amides of aza-lactones prepared from the natural material established that the polyazamacrolides have the (R)-configuration at all stereogenic centers.