(2S,5S,3E)-O-tert-butyldimethylsilyl-6-methyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]hept-3-en-2-ol

Base Information

Chemical Name:(2S,5S,3E)-O-tert-butyldimethylsilyl-6-methyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]hept-3-en-2-ol
CAS No.:405933-50-8
Molecular Formula:C₂₃H₄₁NO₃SSi
Molecular Weight:439.735
Hs Code.:

Synonyms:(2S,5S,3E)-O-tert-butyldimethylsilyl-6-methyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]hept-3-en-2-ol

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Chemical Property of (2S,5S,3E)-O-tert-butyldimethylsilyl-6-methyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]hept-3-en-2-ol

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Technology Process of (2S,5S,3E)-O-tert-butyldimethylsilyl-6-methyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]hept-3-en-2-ol

There total 6 articles about (2S,5S,3E)-O-tert-butyldimethylsilyl-6-methyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]hept-3-en-2-ol 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: 52.0%

: 405933-36-0
(2S,5S,3Z)-3-bromo-O-tert-butyldimethylsilyl-6-methyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]hept-3-en-2-ol

: 405933-50-8
(2S,5S,3E)-O-tert-butyldimethylsilyl-6-methyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]hept-3-en-2-ol

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 16h; Heating;
DOI:10.1021/jo016320y

Reference yield:

: 139192-50-0
(2S)-N-(2,4,6-trimethylbenzenesulfonyl)-2-amino-3-methyl-butanol

: 405933-50-8
(2S,5S,3E)-O-tert-butyldimethylsilyl-6-methyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]hept-3-en-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: (COCl)2; DMSO; diisopropylethylamine / CH₂Cl₂ / -78 - 0 °C

2.1: 7.43 g / CHCl₃ / 0 °C

3.1: Br₂; 1-hexene / CH₂Cl₂ / -78 - 20 °C

3.2: 75 percent / DABCO / CH₂Cl₂ / 0 °C

4.1: DIBAL-H / CHCl₃; toluene / -78 °C

5.1: 34 percent / imidazole / dimethylformamide / 3 h / 20 °C

6.1: 52 percent / Bu₃SnH; AIBN / benzene / 16 h / Heating

With 1H-imidazole; 1-hexene; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); bromine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jo016320y

Reference yield:

: 148838-43-1
N-((S)-1-Formyl-2-methyl-propyl)-2,4,6-trimethyl-benzenesulfonamide

: 405933-50-8
(2S,5S,3E)-O-tert-butyldimethylsilyl-6-methyl-5-[N-(2,4,6-trimethylphenylsulfonyl)amino]hept-3-en-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 7.43 g / CHCl₃ / 0 °C

2.1: Br₂; 1-hexene / CH₂Cl₂ / -78 - 20 °C

2.2: 75 percent / DABCO / CH₂Cl₂ / 0 °C

3.1: DIBAL-H / CHCl₃; toluene / -78 °C

4.1: 34 percent / imidazole / dimethylformamide / 3 h / 20 °C

5.1: 52 percent / Bu₃SnH; AIBN / benzene / 16 h / Heating

With 1H-imidazole; 1-hexene; 2,2'-azobis(isobutyronitrile); bromine; tri-n-butyl-tin hydride; diisobutylaluminium hydride; In dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jo016320y