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

Base Information

• Chemical Name: (2R,3S)-2-(tert-Butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]butane-1,4-diol
• CAS No.: 348584-25-8
• Molecular Formula: C₁₇H₃₁NO₅SSi
• Molecular Weight: 389.588
• Mol file: 348584-25-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3S)-2-(tert-Butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]butane-1,4-diol (348584-25-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 1H-imidazole; sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; ethanol; 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)-3-[(4-methylphenyl)sulfonylamino]butane-1,4-diol (348584-25-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1055/s-2001-12359

upstream raw materials:

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

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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