(2S,3S)-2-(para-toluenesulfonylamino)-3-methyl-5-trimethylsilylpent-4-ynoic acid

Base Information

• Chemical Name: (2S,3S)-2-(para-toluenesulfonylamino)-3-methyl-5-trimethylsilylpent-4-ynoic acid
• CAS No.: 161529-09-5
• Molecular Formula: C₁₆H₂₃NO₄SSi
• Molecular Weight: 353.514
• Mol file: 161529-09-5.mol

Synonyms:(2S,3S)-2-(para-toluenesulfonylamino)-3-methyl-5-trimethylsilylpent-4-ynoic acid

Chemical Property of (2S,3S)-2-(para-toluenesulfonylamino)-3-methyl-5-trimethylsilylpent-4-ynoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-(para-toluenesulfonylamino)-3-methyl-5-trimethylsilylpent-4-ynoic acid

There total 4 articles about (2S,3S)-2-(para-toluenesulfonylamino)-3-methyl-5-trimethylsilylpent-4-ynoic acid 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: 70.0%

(2S,3S)-N-para-toluenesulfonyl-3-methylaziridine-2-carboxylic acid (88452-79-3) + trimethylsilylacetylene (1066-54-2) → (2S,3S)-2-(para-toluenesulfonylamino)-3-methyl-5-trimethylsilylpent-4-ynoic acid (161529-09-5)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

(2S,3S)-N-para-toluenesulfonyl-3-methylaziridine-2-carboxylic acid; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 3h; Further stages.;

DOI:10.1039/b605026n

Reference yield:

methyl (2S,3S)-3-methyl-1-[(4-methylphenyl)sulfonyl]aziridne-2-carboxylate (43188-65-4) → (2S,3S)-2-(para-toluenesulfonylamino)-3-methyl-5-trimethylsilylpent-4-ynoic acid (161529-09-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / aq. NaOH / tetrahydrofuran / 3 h / 20 °C

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

2.2: 70 percent / hexane; tetrahydrofuran / 3 h / 0 - 20 °C

With sodium hydroxide; n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1039/b605026n

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (2S,3S)-2-(para-toluenesulfonylamino)-3-methyl-5-trimethylsilylpent-4-ynoic acid (161529-09-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 600 mg / H₂O; ethyl acetate / 20 h / 20 °C

2.1: 100 percent / aq. NaOH / tetrahydrofuran / 3 h / 20 °C

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

3.2: 70 percent / hexane; tetrahydrofuran / 3 h / 0 - 20 °C

With sodium hydroxide; n-butyllithium; In tetrahydrofuran; hexane; water; ethyl acetate;

DOI:10.1039/b605026n

upstream raw materials:

lithium trimethylsilylacetylenide

(2S,3S)-N-para-toluenesulfonyl-3-methylaziridine-2-carboxylic acid

trimethylsilylacetylene

methyl (2S,3S)-3-methyl-1-[(4-methylphenyl)sulfonyl]aziridne-2-carboxylate

Downstream raw materials:

(2S,3S)-2-(para-toluenesulfonylamino)-3-methylpent-4-ynoic acid

(2S,3S) methyl 3-methyl-2-(4-methylphenylsulfonamido)pentanoate

methyl (2S,3S)-2-(para-toluenesulfonylamino)-3-methylpent-4-ynoate