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

Base Information

• Chemical Name: (2S,3S)-2-[N-(2,4,6-Trimethylphenylsulfonyl)amino]-5-trimethylsilylpent-4-yne-1,3-diol
• CAS No.: 253676-18-5
• Molecular Formula: C₁₇H₂₇NO₄SSi
• Molecular Weight: 369.557
• Mol file: 253676-18-5.mol

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

Chemical Property of (2S,3S)-2-[N-(2,4,6-Trimethylphenylsulfonyl)amino]-5-trimethylsilylpent-4-yne-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-[N-(2,4,6-Trimethylphenylsulfonyl)amino]-5-trimethylsilylpent-4-yne-1,3-diol

There total 1 articles about (2S,3S)-2-[N-(2,4,6-Trimethylphenylsulfonyl)amino]-5-trimethylsilylpent-4-yne-1,3-diol 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: 62.0%

2-mesitylenesulphonyl chloride (773-64-8) + (3S,4S)-4-[N-(tert-Butoxycarbonyl)amino]-5-(tert-butyldimethylsiloxy)-1-trimethylsilylpent-1-yn-3-ol (253676-15-2) → (2S,3S)-2-[N-(2,4,6-Trimethylphenylsulfonyl)amino]-5-trimethylsilylpent-4-yne-1,3-diol (253676-18-5) + (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-ol (253676-17-4)

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: 83.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3S)-2-[N-(2,4,6-Trimethylphenylsulfonyl)amino]-5-trimethylsilylpent-4-yne-1,3-diol (253676-18-5) → (3S,4S)-5-(tert-Butyldimethylsiloxy)-4-[N-(2,4,6-trimethylphenylsulfonyl)amino]-1-trimethylsilylpent-1-yn-3-ol (253676-17-4)

Guidance literature:

With 1H-imidazole; In chloroform; N,N-dimethyl-formamide; at 0 ℃; for 2h;

DOI:10.1039/a905027b

Reference yield:

(2S,3S)-2-[N-(2,4,6-Trimethylphenylsulfonyl)amino]-5-trimethylsilylpent-4-yne-1,3-diol (253676-18-5) → (2R,3R)-3-[(tert-Butyldimethylsiloxy)methyl]-2-ethynyl-N-(2,4,6-trimethylphenylsulfonyl)aziridine (253676-34-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / imidazole / dimethylformamide; CHCl₃ / 2 h / 0 °C

2: 90 percent / NaOMe / methanol / 4.5 h / 20 °C

3: 96 percent / diethyl azodicarboxylate; Ph₃P / tetrahydrofuran; toluene / 0.5 h / 0 °C

With 1H-imidazole; sodium methylate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: Substitution / 3: Cyclization;

DOI:10.1039/a905027b

upstream raw materials:

2-mesitylenesulphonyl chloride

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

Downstream raw materials:

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

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

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