(3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-ol

Base Information

Chemical Name:(3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-ol
CAS No.:253676-17-4
Molecular Formula:C₂₃H₄₁NO₄SSi₂
Molecular Weight:483.82
Hs Code.:

Synonyms:(3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-ol

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Chemical Property of (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-ol

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Technology Process of (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-ol

There total 5 articles about (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-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: 83.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 253676-18-5
(2S,3S)-2-[N-(2,4,6-Trimethylphenylsulfonyl)amino]-5-trimethylsilylpent-4-yne-1,3-diol

: 253676-17-4
(3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-ol

Guidance literature:: With 1H-imidazole; In chloroform; N,N-dimethyl-formamide; at 0 ℃; for 2h;
DOI:10.1039/a905027b

Reference yield: 62.0%

: 773-64-8
2-mesitylenesulphonyl chloride

: 253676-15-2
(3S,4S)-4-[N-(tert-Butoxycarbonyl)amino]-5-(tert-butyldimethylsiloxy)-1-trimethylsilylpent-1-yn-3-ol

: 253676-18-5
(2S,3S)-2-[N-(2,4,6-Trimethylphenylsulfonyl)amino]-5-trimethylsilylpent-4-yne-1,3-diol

: 253676-17-4
(3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-ol

Guidance literature:: (3S,4S)-4-[N-(tert-Butoxycarbonyl)amino]-5-(tert-butyldimethylsiloxy)-1-trimethylsilylpent-1-yn-3-ol; With trifluoroacetic acid; In chloroform; at 0 ℃; for 1h;

2-mesitylenesulphonyl chloride; With triethylamine; In chloroform; at 0 ℃; for 1h;
DOI:10.1039/a905027b

Reference yield:

: 126645-26-9
(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate

: 253676-17-4
(3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: DIBAL-H / toluene / 1 h / -78 °C

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

2.2: tetrahydrofuran; hexane / 1 h / -78 °C

3.1: TFA / CHCl₃ / 1 h / 0 °C

3.2: 62 percent / Et₃N / CHCl₃ / 1 h / 0 °C

With n-butyllithium; diisobutylaluminium hydride; trifluoroacetic acid; In tetrahydrofuran; hexane; chloroform; toluene; 1.1: Reduction / 2.1: Metallation / 2.2: Addition / 3.1: Substitution / 3.2: Substitution;
DOI:10.1039/a905027b