934472-06-7

Basic information

• Product Name: 2-hydroxyethyl-1-(toluene-4-sulfonyl)aziridine
• Synonyms: 2-hydroxyethyl-1-(toluene-4-sulfonyl)aziridine
• CAS NO: 934472-06-7
• Molecular Weight: 241.311
• Mol File: 934472-06-7.mol

Chemical Properties

• CAS DataBase Reference: 2-hydroxyethyl-1-(toluene-4-sulfonyl)aziridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxyethyl-1-(toluene-4-sulfonyl)aziridine(934472-06-7)
• EPA Substance Registry System: 2-hydroxyethyl-1-(toluene-4-sulfonyl)aziridine(934472-06-7)

Safety Data

• Hazardous Substances Data: 934472-06-7(Hazardous Substances Data)

Upstream product

• 95331-51-4 N-[(4-methylphenyl)sulfonyl]-L-aspartic acid 1,4-dimethyl ester 
• 1360584-10-6 C₁₁H₁₄ClNO₃S 
• 1360584-01-5 N-(2-chloro-1-(phenylsulfonyl)ethyl)-p-toluenesulfonamide 
• 873-55-2 sodium benzenesulfonate 
• 616866-44-5 (2R)-N-(p-toluenesulfonyl)-aspartic acid dimethyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 147136-78-5 N-(3-hydroxy-1-hydroxymethyl-propyl)-4-methylbenzenesulfonamide 

Downstream Products

• 1334404-52-2 2-allyl-6-(2-hydroxyethyl)-1-(toluene-4-sulfonyl)-piperidin-3-ol 
• 1334404-51-1 2-allyl-6-[2-((tert-butyl)diphenylsilanyloxy)ethyl]-1-(toluene-4-sulfonyl)-piperidin-3-ol 
• 1334404-53-3 (-)-(1R,3S,6S)-3-(2-((tert-butyl)diphenylsilyloxy)ethyl)-2-tosyl-2-azabicyclo[4.1.0]heptane 
• 1334404-54-4 (+)-(1S,2R,5S)-2-bromo-2-(bromomethyl)-9-tosyl-8-oxa-9-aza-bicyclo[3.3.1]nonane 
• 1334404-55-5 (-)-2-((1R,3S,6S)-2-tosyl-2-azabicyclo[4.1.0]heptan-3-yl)ethanol 
• 1334404-56-6 (2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-(iodomethyl)-2-methoxy-1-tosylpiperidine 
• 1334404-58-8 (-)-(E)-methyl 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)but-2-enoate 
• 1334404-60-2 4-((2S,3R,6S)-6-(2-((tert-butyl)diphenylsilyloxy)ethyl)-3-methyl-1-tosylpiperidin-2-yl)butan-1-ol 
• 1334404-41-9 C₃₁H₄₁NO₄SSi 
• 1334404-44-2 (R)-N-(1-[2-((tert-butyl)diphenylsilanyloxy)ethyl]-4-[1,3]dioxolan-2-ylbutyl)-4-methylbenzenesulfonamide 
• 1334404-42-0 2-(((tert-butyl)diphenylsilanoxy)ethyl)-5-methylene-1-(toluene-4-sulfonyl)piperidine 
• 1334404-45-3 2-[2-((tert-butyl)diphenylsilanyloxy)ethyl]-1-(toluene-4-sulfonyl)-1,2,3,4-tetrahydropyridine 
• 1334404-57-7 C₃₂H₄₃NO₄SSi 
• 1334404-59-9 C₃₆H₄₉NO₅SSi 

Relevant articles and documents

Stereoselective approaches to 2,3,6-trisubstituted piperidines. An enantiospecific synthesis of quinolizidine (-)-217A

The enantiospecific and diastereocontrolled total synthesis of alkaloid (-)-217A is described that employs a stepwise [3+3] annelation strategy and a piperidine 2,3-cyclopropanation-ring opening reaction as the key steps.

One-pot synthesis of chiral aziridines by a domino reaction by using desulfonylative formation on the n-tosyl imine of chloroacetaldehyde with an asymmetric mannich reaction as a key step

Aziridines with ease: A one-pot synthesis of chiral aziridine derivatives with excellent diastereo- and enantioselectivities was developed through uninterrupted sequential reactions, including desulfonylative formation of the N-Ts imine derived from chloroacetaldehyde, a diarylprolinol silyl ether mediated asymmetric Mannich reaction, reduction, and aziridine formation (see scheme; Ts=tosyl).

An efficient approach to 2-substituted N-tosylpiperdines: asymmetric synthesis of 2-(2-hydroxy substituted)piperidine alkaloids

We have developed an efficient and a general approach to chiral 2-substituted N-tosylpiperidines starting from chiral α-substituted-N-tosylaziridines. Using this approach, we have synthesized (+)-coniine. The synthesis of chiral N-tosyl-2-piperidinylethanol 15 and ent-15, was achieved from l- and d-aspartic acids, respectively in few steps. Piperidine 15 was converted into 2-(2-hydroxysubstituted)piperidines of type 2 in optically active form. By applying this strategy, asymmetric syntheses of halosaline (R,R)-2a, (+)- and (-)-sedamine 2b, (+)- and (-)-allosedamine 2c, (+)- and (-)-sedridine 2d, (+)- and (-)-allosedridine 2e, (+)-tetraponerine T-3 3a, T-4 3c, T-7 3b, and T-8 3d have been achieved in high yields. These stereoisomers can be interconverted via Mitsunobu inversion in excellent yields.