(2R,3S)-3-Benzyl-2-(1-bromovinyl)-N-(2,4,6-trimethylphenylsulfonyl)aziridine

Base Information

Chemical Name:(2R,3S)-3-Benzyl-2-(1-bromovinyl)-N-(2,4,6-trimethylphenylsulfonyl)aziridine
CAS No.:253676-03-8
Molecular Formula:C₂₀H₂₂BrNO₂S
Molecular Weight:420.37
Hs Code.:

Synonyms:(2R,3S)-3-Benzyl-2-(1-bromovinyl)-N-(2,4,6-trimethylphenylsulfonyl)aziridine

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Chemical Property of (2R,3S)-3-Benzyl-2-(1-bromovinyl)-N-(2,4,6-trimethylphenylsulfonyl)aziridine

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Technology Process of (2R,3S)-3-Benzyl-2-(1-bromovinyl)-N-(2,4,6-trimethylphenylsulfonyl)aziridine

There total 9 articles about (2R,3S)-3-Benzyl-2-(1-bromovinyl)-N-(2,4,6-trimethylphenylsulfonyl)aziridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 220324-15-2
(4S,2Z)-2-Bromo-O-methylsulfonyl-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol

: (2S,3S)-3-Benzyl-2-(1-bromovinyl)-N-(2,4,6-trimethylphenylsulfonyl)aziridine

: 253676-03-8
(2R,3S)-3-Benzyl-2-(1-bromovinyl)-N-(2,4,6-trimethylphenylsulfonyl)aziridine

Guidance literature:: With sodium hydride; dimethyl sulfoxide; at 30 ℃; for 2.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1016/S0957-4166(98)00406-6

Reference yield:

: 220324-06-1
Methyl (4S,2Z)-2-bromo-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-enoate

: 253676-03-8
(2R,3S)-3-Benzyl-2-(1-bromovinyl)-N-(2,4,6-trimethylphenylsulfonyl)aziridine

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / DIBAL-H / toluene; CHCl₃ / 3 h / -78 - -20 °C

2: 94 percent / Et₃N / tetrahydrofuran / 1 h / -78 - 0 °C

3: NaH; DMSO / 2.5 h / 30 °C

With sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; chloroform; toluene; 1: Reduction / 2: Esterification / 3: Cyclization;
DOI:10.1039/a905027b

Reference yield:

: 220324-10-7
(4S,2Z)-2-Bromo-5-phenyl-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-2-en-1-ol

: 253676-03-8
(2R,3S)-3-Benzyl-2-(1-bromovinyl)-N-(2,4,6-trimethylphenylsulfonyl)aziridine

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / Et₃N / tetrahydrofuran / 1 h / -78 - 0 °C

2: NaH; DMSO / 2.5 h / 30 °C

With sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1: Esterification / 2: Cyclization;
DOI:10.1039/a905027b