(E)-N,N-bis(tert-butoxycarbonyl)-3-[(tert-butyldimethylsilyl)oxy]-5-(phenylsulfonyl)pent-4-en-1-amine

Base Information

Chemical Name:(E)-N,N-bis(tert-butoxycarbonyl)-3-[(tert-butyldimethylsilyl)oxy]-5-(phenylsulfonyl)pent-4-en-1-amine
CAS No.:208333-12-4
Molecular Formula:C₂₇H₄₅NO₇SSi
Molecular Weight:555.808
Hs Code.:

Synonyms:(E)-N,N-bis(tert-butoxycarbonyl)-3-[(tert-butyldimethylsilyl)oxy]-5-(phenylsulfonyl)pent-4-en-1-amine

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Chemical Property of (E)-N,N-bis(tert-butoxycarbonyl)-3-[(tert-butyldimethylsilyl)oxy]-5-(phenylsulfonyl)pent-4-en-1-amine

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Technology Process of (E)-N,N-bis(tert-butoxycarbonyl)-3-[(tert-butyldimethylsilyl)oxy]-5-(phenylsulfonyl)pent-4-en-1-amine

There total 8 articles about (E)-N,N-bis(tert-butoxycarbonyl)-3-[(tert-butyldimethylsilyl)oxy]-5-(phenylsulfonyl)pent-4-en-1-amine 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: 96.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 197142-52-2
(E)-5-[N,N-bis(tert-butoxycarbonyl)amino]-1-(phenylsulfonyl)pent-1-en-3-ol

: 208333-12-4
(E)-N,N-bis(tert-butoxycarbonyl)-3-[(tert-butyldimethylsilyl)oxy]-5-(phenylsulfonyl)pent-4-en-1-amine

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃;
DOI:10.1021/jo972167p

Reference yield:

: 3112-85-4
methylphenylsulfonate

: 208333-12-4
(E)-N,N-bis(tert-butoxycarbonyl)-3-[(tert-butyldimethylsilyl)oxy]-5-(phenylsulfonyl)pent-4-en-1-amine

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 93 percent / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: 99 percent / m-CPBA / CH₂Cl₂ / 0.25 h / -78 °C

3.1: 94 percent / piperidine / CH₂Cl₂ / 10 h / 0 °C

4.1: 96 percent / imidazole / CH₂Cl₂ / 20 °C

With piperidine; 1H-imidazole; n-butyllithium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; 1.1: Metallation / 1.2: sulfenylation / 2.1: Oxidation / 3.1: Condensation / 4.1: silylation;
DOI:10.1021/jo972167p

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 208333-12-4
(E)-N,N-bis(tert-butoxycarbonyl)-3-[(tert-butyldimethylsilyl)oxy]-5-(phenylsulfonyl)pent-4-en-1-amine

Guidance literature:: Multi-step reaction with 5 steps

1: CH₂Cl₂ / 0.5 h / 0 - 20 °C

2: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

3: 16 g / aq. AcOH / 6 h / 20 °C

4: 94 percent / piperidine / CH₂Cl₂ / 10 h / 0 °C

5: 96 percent / imidazole / CH₂Cl₂ / 20 °C

With piperidine; 1H-imidazole; n-butyllithium; acetic acid; In tetrahydrofuran; hexane; dichloromethane; 1: Acylation / 2: Acylation / 3: Hydrolysis / 4: Condensation / 5: silylation;
DOI:10.1021/jo972167p