Dimethyl (2R,3R)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate

Base Information

• Chemical Name: Dimethyl (2R,3R)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate
• CAS No.: 348584-17-8
• Molecular Formula: C₁₉H₃₁NO₇SSi
• Molecular Weight: 445.609
• Mol file: 348584-17-8.mol

Synonyms:Dimethyl (2R,3R)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate

Chemical Property of Dimethyl (2R,3R)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Dimethyl (2R,3R)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate

There total 1 articles about Dimethyl (2R,3R)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate 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: 85.0%

tert-butyldimethylsilyl chloride (18162-48-6) + dimethyl (2R,3R)-N-(p-toluenesulfonyl)-3-amino-2-hydroxysuccinate (176435-38-4) → Dimethyl (2R,3R)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate (348584-17-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 35 ℃; for 16h;

DOI:10.1055/s-2001-12359

Reference yield: 99.0%

Dimethyl (2R,3R)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate (348584-17-8) → (2R,3S)-2-(tert-Butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]butane-1,4-diol (348584-25-8)

Guidance literature:

With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol; at 20 ℃; for 2h;

DOI:10.1055/s-2001-12359

Reference yield:

Dimethyl (2R,3R)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate (348584-17-8) → (2S)-1-[(4-Methylphenyl)sulfonyl]-2-[(2R)-oxiran-2-yl]aziridine

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / CaCl₂; NaBH₄ / ethanol; tetrahydrofuran / 2 h / 20 °C

2: 97 percent / Et₃N; Me₃N*HCl / CH₂Cl₂ / 20 °C

3: 65 percent / TBAF*3H₂O / tetrahydrofuran / 16 h / 20 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; trimethylamine hydrochloride; triethylamine; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1055/s-2001-12359

upstream raw materials:

tert-butyldimethylsilyl chloride

dimethyl (2R,3R)-N-(p-toluenesulfonyl)-3-amino-2-hydroxysuccinate

Downstream raw materials:

(2R,3S)-2-(tert-Butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]butane-1,4-diol

(2R,3S)-2-(tert-Butyldimethylsiloxy)-1,4-bis[(4-methylphenyl)sulfonyloxy]-3-[(4-methylphenyl)sulfonylamino]butane