2-(toluene-4-sulfonylamino)-5-trimethylsilanyl-pent-4-ynoic acid ethyl ester

Base Information

• Chemical Name: 2-(toluene-4-sulfonylamino)-5-trimethylsilanyl-pent-4-ynoic acid ethyl ester
• CAS No.: 271598-95-9
• Molecular Formula: C₁₇H₂₅NO₄SSi
• Molecular Weight: 367.541
• Mol file: 271598-95-9.mol

Synonyms:2-(toluene-4-sulfonylamino)-5-trimethylsilanyl-pent-4-ynoic acid ethyl ester

Chemical Property of 2-(toluene-4-sulfonylamino)-5-trimethylsilanyl-pent-4-ynoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(toluene-4-sulfonylamino)-5-trimethylsilanyl-pent-4-ynoic acid ethyl ester

There total 3 articles about 2-(toluene-4-sulfonylamino)-5-trimethylsilanyl-pent-4-ynoic acid ethyl ester 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: 77.0%

p-toluenesulfonyl chloride (98-59-9) + 2-(benzhydrylidene-amino)-5-trimethylsilanyl-pent-4-ynoic acid ethyl ester (271598-87-9) → ethyl 2-{[(4-methylphenyl)sulfonyl]amino}pent-4-ynoate (271598-92-6) + 2-(toluene-4-sulfonylamino)-5-trimethylsilanyl-pent-4-ynoic acid ethyl ester (271598-95-9)

Guidance literature:

2-(benzhydrylidene-amino)-5-trimethylsilanyl-pent-4-ynoic acid ethyl ester; With hydrogenchloride; water; In diethyl ether;

p-toluenesulfonyl chloride; With triethylamine; In dichloromethane; Further stages.;

DOI:10.1039/a910217p

Reference yield:

3-bromo-1-(trimethylsilyl)-1-propyne (38002-45-8) → 2-(toluene-4-sulfonylamino)-5-trimethylsilanyl-pent-4-ynoic acid ethyl ester (271598-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / K₂CO₃ / acetonitrile

2.1: HCl; H₂O / diethyl ether

2.2: 77 percent / Et₃N / CH₂Cl₂

With hydrogenchloride; water; potassium carbonate; In diethyl ether; acetonitrile; 1.1: Alkylation / 2.1: Hydrolysis / 2.2: Tosylation;

DOI:10.1039/a910217p

Reference yield:

(E)-ethyl 2-(tosylimino)acetate (83670-53-5) + 3-tri-n-butylstannyl-1-trimethylsilyl-1-propyne → 2-(toluene-4-sulfonylamino)-5-trimethylsilanyl-pent-4-ynoic acid ethyl ester (271598-95-9) + (R)-2-(Toluene-4-sulfonylamino)-3-trimethylsilanyl-penta-3,4-dienoic acid ethyl ester + (S)-2-(Toluene-4-sulfonylamino)-3-trimethylsilanyl-penta-3,4-dienoic acid ethyl ester

Guidance literature:

With (R)-2,2'-bis[bis(3-methylphenyl)phosphino]-1,1'-binaphthyl; tetrakis(acetonitrile)copper(I) perchlorate; In diethyl ether; at -30 ℃; for 24h; Title compound not separated from byproducts;

DOI:10.1246/cl.2002.298

upstream raw materials:

p-toluenesulfonyl chloride

2-(benzhydrylidene-amino)-5-trimethylsilanyl-pent-4-ynoic acid ethyl ester

(E)-ethyl 2-(tosylimino)acetate

3-bromo-1-(trimethylsilyl)-1-propyne

Downstream raw materials:

ethyl 2-{[(4-methylphenyl)sulfonyl](5-trimethylsilylprop-2-enyl)amino}pent-4-ynoate