methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazolidine-4-carboxylate

Base Information

• Chemical Name: methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazolidine-4-carboxylate
• CAS No.: 292073-45-1
• Molecular Formula: C₂₅H₃₅NO₃SSi
• Molecular Weight: 457.709
• Mol file: 292073-45-1.mol

Synonyms:methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazolidine-4-carboxylate

Chemical Property of methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazolidine-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazolidine-4-carboxylate

There total 7 articles about methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazolidine-4-carboxylate 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: 98.0%

L-Cysteine methyl ester (2485-62-3) + 3-((tert-butyldiphenylsilyl)oxy)-2,2-dimethylpropanal (136022-55-4) → methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazolidine-4-carboxylate (292073-45-1)

Guidance literature:

L-Cysteine methyl ester; 3-[(tert-butyldiphenylsilyl)oxy]-2,2-dimethylpropanal; With thionyl chloride; In methanol; Inert atmosphere;

With sodium hydrogencarbonate; In methanol; ethanol; water; Inert atmosphere;

DOI:10.1002/ejoc.201100669

Reference yield:

L-cysteine methyl ester hydrochloride (18598-63-5) + 3-((tert-butyldiphenylsilyl)oxy)-2,2-dimethylpropanal (136022-55-4) → methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazolidine-4-carboxylate (292073-45-1)

Guidance literature:

With triethylamine; In toluene; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(03)01020-2

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → methyl 2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazolidine-4-carboxylate (292073-45-1)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 14 h / 20 °C

2: DIBAL / diethyl ether; hexane / 0.5 h / -78 °C

3: Et₃N; pyridine*SO₃; DMSO / CH₂Cl₂ / 0.33 h / 20 °C

4: 16.8 g / Et₃N / toluene / 12 h / 20 °C

With 1H-imidazole; sulfur trioxide pyridine complex; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Parikh-Doering oxidation;

DOI:10.1016/S0040-4020(03)01020-2

upstream raw materials:

L-cysteine methyl ester hydrochloride

3-((tert-butyldiphenylsilyl)oxy)-2,2-dimethylpropanal

Methyl 2,2-dimethyl-3-hydroxypropionate

tert-butylchlorodiphenylsilane

Downstream raw materials:

4-bromomethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole

4-hydroxymethyl-2-[(2-tert-butyldimethylsilyloxy)-1,1-dimethylethyl]thiazole

4-((2E)-4-bromobut-2-enyl)-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazole

(2E)-4-{2-[2-(tert-butyldiphenylsilyloxy)-1,1-dimethylethyl]thiazol-4-yl}but-2-en-1-ol