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

Base Information

• Chemical Name: (2R,3S)-2-(tert-Butyldimethylsiloxy)-1,4-bis[(4-methylphenyl)sulfonyloxy]-3-[(4-methylphenyl)sulfonylamino]butane
• CAS No.: 348584-35-0
• Molecular Formula: C₃₁H₄₃NO₉S₃Si
• Molecular Weight: 697.967
• Mol file: 348584-35-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (2R,3S)-2-(tert-Butyldimethylsiloxy)-1,4-bis[(4-methylphenyl)sulfonyloxy]-3-[(4-methylphenyl)sulfonylamino]butane 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: 97.0%

p-toluenesulfonyl chloride (98-59-9) + (2R,3S)-2-(tert-Butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]butane-1,4-diol (348584-25-8) → (2R,3S)-2-(tert-Butyldimethylsiloxy)-1,4-bis[(4-methylphenyl)sulfonyloxy]-3-[(4-methylphenyl)sulfonylamino]butane (348584-35-0)

Guidance literature:

With trimethylamine hydrochloride; triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1055/s-2001-12359

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3S)-2-(tert-Butyldimethylsiloxy)-1,4-bis[(4-methylphenyl)sulfonyloxy]-3-[(4-methylphenyl)sulfonylamino]butane (348584-35-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / imidazole / dimethylformamide / 16 h / 35 °C

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

3: 97 percent / Et₃N; Me₃N*HCl / CH₂Cl₂ / 20 °C

With 1H-imidazole; sodium tetrahydroborate; trimethylamine hydrochloride; triethylamine; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2001-12359

Reference yield:

dimethyl (2R,3R)-N-(p-toluenesulfonyl)-3-amino-2-hydroxysuccinate (176435-38-4) → (2R,3S)-2-(tert-Butyldimethylsiloxy)-1,4-bis[(4-methylphenyl)sulfonyloxy]-3-[(4-methylphenyl)sulfonylamino]butane (348584-35-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / imidazole / dimethylformamide / 16 h / 35 °C

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

3: 97 percent / Et₃N; Me₃N*HCl / CH₂Cl₂ / 20 °C

With 1H-imidazole; sodium tetrahydroborate; trimethylamine hydrochloride; triethylamine; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2001-12359

upstream raw materials:

p-toluenesulfonyl chloride

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

tert-butyldimethylsilyl chloride

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