167029-47-2

Usage

Chemical compound

2-Aziridinemethanol, 1-[(4-methylphenyl)sulfonyl]-3-phenyl-, (2R,3R)
Derivative of aziridinemethanol
Contains a sulfonyl group attached to a phenyl ring and a methyl group

Stereochemistry

(2R,3R)
Potential applications in organic synthesis and pharmaceutical research
Unique structure and properties
Reactivity and potential biological effects should be considered when working with 2-Aziridinemethanol, 1-[(4-methylphenyl)sulfonyl]-3-phenyl-, (2R,3R)- in a laboratory setting

Upstream product

• 167502-75-2 (1S,2S)-3-tert-butyldimethylsilyloxy-2-(4-methylphenyl)sulfonamido-1-phenyl1-propanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 929722-25-8 (3-phenyl-aziridin-2-yl)-methanol 
• 167613-42-5 (2R,3R)-2-(tert-butyldimethylsiloxy)methyl-3-phenyl-1-<(4-methylphenyl)sulfonyl>aziridine 

Downstream Products

• 171358-28-4 (3R,4R)-3-hydroxy-4-(4-methylphenyl)sulfonylamino-4-phenylbutanenitrile 
• 929722-26-9 C₁₇H₁₉NO₃S 
• 167029-48-3 (2S,3R)-3-Amino-1,2-epoxy-N-<(4-methylphenyl)sulfonyl>-3-phenylpropane 
• 169870-31-9 methyl (4S,5R,2E)-4,5-epimino-5-phenyl-N-<(4-methylphenyl)sulfonyl>pent-2-enoate 
• 169870-32-0 methyl (4S,5R,2Z)-4,5-epimino-N-(4-methylphenyl)sulfonyl-5-phenylpent-2-enoate 
• 171358-29-5 (3R,4R)-3-hydroxy-4-(4-methylphenyl)sulfonylamino-4-phenylbutanamide 

Relevant academic research and scientific papers

Synthesis of N-heterocycles, beta-amino acids, and allyl amines via aza-payne mediated reaction of ylides and hydroxy aziridines

An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under the basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring closure yields the desired pyrrolidine, thus completing the relay of the 3-membered the 5-membered nitrogen containing ring system. This process takes place with complete transfer of stereochemical fidelity, and can be applied to sterically hindered aziridinols.

Diastereomerically and enantiomerically pure 2,3-disubstituted pyrrolidines from 2,3-aziridin-1-ols using a sulfoxonium ylide: A one-carbon homologative relay ring expansion

An ylide-based aza-Payne rearrangement of 2,3-aziridin-1-ols leads to an efficient process for the preparation of pyrrolidines. The aza-Payne rearrangement under basic reaction conditions favors the formation of epoxy amines. Subsequent nucleophilic attack of the epoxide by the ylide yields a bis-anion, which upon a 5-exo-tet ring-closure yields the desired pyrrolidine, thus completing the relay of the three-membered to the five-membered nitrogen-containing ring system. This process takes place with complete transfer of stereochemical fidelity and can be applied to sterically hindered aziridinols.

Solution- and solid-phase synthesis of 4-hydroxy-4,5-dihydroisoxazole serivatives from enantiomerically pure N-tosyl-2,3-aziridine alcohols

(formula presented) Enantiomerically pure N-tosyl-2,3-aziridine alcohols are directly converted into 4-hydroxy-4,5-dihydroisoxazole 2-oxides through oxidation to the corresponding aldehydes followed by in situ tandem nitroaldol-intramolecular cyclization.

Synthesis of optically pure 2-Aziridinemethanols: Versatile synthetic building blocks

Synthesis of three cis-trans pairs of N-sulfonylated-2-aziridinemethanols starting from (S)-threonine, (R)-allothreonine, a chiral 2-amino alcohol, or enantiomerically enriched 2,3-epoxy alcohols is described. A synthetic route to N-tosyl- and N-mesyl-2-a