(2S,3S)-3-Isopropyl-2-[2-(methoxycarbonyl)ethynyl]-N-(2,4,6-trimethylphenylsulfonyl)aziridine

Base Information

Chemical Name:(2S,3S)-3-Isopropyl-2-[2-(methoxycarbonyl)ethynyl]-N-(2,4,6-trimethylphenylsulfonyl)aziridine
CAS No.:253676-37-8
Molecular Formula:C₁₈H₂₃NO₄S
Molecular Weight:349.451
Hs Code.:

Synonyms:(2S,3S)-3-Isopropyl-2-[2-(methoxycarbonyl)ethynyl]-N-(2,4,6-trimethylphenylsulfonyl)aziridine

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Chemical Property of (2S,3S)-3-Isopropyl-2-[2-(methoxycarbonyl)ethynyl]-N-(2,4,6-trimethylphenylsulfonyl)aziridine

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Technology Process of (2S,3S)-3-Isopropyl-2-[2-(methoxycarbonyl)ethynyl]-N-(2,4,6-trimethylphenylsulfonyl)aziridine

There total 5 articles about (2S,3S)-3-Isopropyl-2-[2-(methoxycarbonyl)ethynyl]-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: 71.0%

: 79-22-1
methyl chloroformate

: 220765-48-0
(2S,3S)-2-ethynyl-3-isopropyl-N-(2,4,6-trimethyl-phenylsulfonyl)-aziridine

: 253676-37-8
(2S,3S)-3-Isopropyl-2-[2-(methoxycarbonyl)ethynyl]-N-(2,4,6-trimethylphenylsulfonyl)aziridine

Guidance literature:: (2S,3S)-2-ethynyl-3-isopropyl-N-(2,4,6-trimethyl-phenylsulfonyl)-aziridine; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

methyl chloroformate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1039/a905027b

Reference yield:

: 773-64-8
2-mesitylenesulphonyl chloride

: 253676-37-8
(2S,3S)-3-Isopropyl-2-[2-(methoxycarbonyl)ethynyl]-N-(2,4,6-trimethylphenylsulfonyl)aziridine

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N / CHCl₃ / 1 h / 0 °C

2.1: 83 percent / TBAF / tetrahydrofuran / 0.25 h / 0 °C

3.1: 98 percent / diethyl azodicarboxylate; Ph₃P / tetrahydrofuran; toluene / 0.5 h / 0 °C

4.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 71 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

With tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; hexane; chloroform; toluene; 1.1: Substitution / 2.1: Substitution / 3.1: Cyclization / 4.1: Metallation / 4.2: Acylation;
DOI:10.1039/a905027b

Reference yield:

: (3S)-2-(1-Bromovinyl)-3-isopropyl-N-(2,4,6-trimethylphenylsulfonyl)aziridine

: 253676-37-8
(2S,3S)-3-Isopropyl-2-[2-(methoxycarbonyl)ethynyl]-N-(2,4,6-trimethylphenylsulfonyl)aziridine

Guidance literature:: Multi-step reaction with 2 steps

1.1: 74 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - 0 °C

2.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 71 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

With potassium tert-butylate; lithium diisopropyl amide; In tetrahydrofuran; hexane; 1.1: Dehydrobromination / 2.1: Metallation / 2.2: Acylation;
DOI:10.1039/a905027b