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

Base Information

• Chemical Name: (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-1-yn-3-ol
• CAS No.: 253676-19-6
• Molecular Formula: C₂₀H₃₃NO₄SSi
• Molecular Weight: 411.638
• Mol file: 253676-19-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-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: 90.0%

(3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-ol (253676-17-4) → (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-1-yn-3-ol (253676-19-6)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 4.5h;

DOI:10.1039/a905027b

Reference yield:

(3S,4S)-4-[N-(tert-Butoxycarbonyl)amino]-5-(tert-butyldimethylsiloxy)-1-trimethylsilylpent-1-yn-3-ol (253676-15-2) → (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-1-yn-3-ol (253676-19-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: TFA / CHCl₃ / 1 h / 0 °C

1.2: 17 percent / Et₃N / CHCl₃ / 1 h / 0 °C

2.1: 83 percent / imidazole / dimethylformamide; CHCl₃ / 2 h / 0 °C

3.1: 90 percent / NaOMe / methanol / 4.5 h / 20 °C

With 1H-imidazole; sodium methylate; trifluoroacetic acid; In methanol; chloroform; N,N-dimethyl-formamide; 1.1: Substitution / 1.2: Substitution / 2.1: Etherification / 3.1: Substitution;

DOI:10.1039/a905027b

Reference yield:

(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate (126645-26-9) → (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]pent-1-yn-3-ol (253676-19-6)

Guidance literature:

Multi-step reaction with 4 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

4.1: 90 percent / NaOMe / methanol / 4.5 h / 20 °C

With n-butyllithium; sodium methylate; diisobutylaluminium hydride; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; chloroform; toluene; 1.1: Reduction / 2.1: Metallation / 2.2: Addition / 3.1: Substitution / 3.2: Substitution / 4.1: Substitution;

DOI:10.1039/a905027b

upstream raw materials:

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

(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate

tert-butyldimethylsilyl chloride

tert-butyl (S)-1-(tert-butyldimethylsilyloxy)-3-oxopropan-2-yl carbamate

Downstream raw materials:

(2R,3R)-3-[(tert-Butyldimethylsiloxy)methyl]-2-ethynyl-N-(2,4,6-trimethylphenylsulfonyl)aziridine