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

Base Information

• Chemical Name: Diethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate
• CAS No.: 348584-20-3
• Molecular Formula: C₂₁H₃₅NO₇SSi
• Molecular Weight: 473.663

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

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

Chemical Property:

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

There total 3 articles about Diethyl (2R,3S)-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: 89.0%

Diethyl (2R,3S)-2-hydroxy-3-[(4-methylphenyl)sulfonylamino]succinate (348594-86-5) + tert-butyldimethylsilyl chloride (18162-48-6) → Diethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate (348584-20-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1055/s-2001-12359

Reference yield:

chloroamine-T (127-65-1) → Diethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate (348584-20-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / H₂O / 2-methyl-propan-2-ol / 168 h

2: 89 percent / imidazole / dimethylformamide

With 1H-imidazole; water; In N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1055/s-2001-12359

Reference yield:

trans-2,3-bis(ethoxycarbonyl)oxirane (74243-85-9) → Diethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-[(4-methylphenyl)sulfonylamino]succinate (348584-20-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / H₂O / 2-methyl-propan-2-ol / 168 h

2: 89 percent / imidazole / dimethylformamide

With 1H-imidazole; water; In N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1055/s-2001-12359

upstream raw materials:

Diethyl (2R,3S)-2-hydroxy-3-[(4-methylphenyl)sulfonylamino]succinate

tert-butyldimethylsilyl chloride

chloroamine-T

trans-2,3-bis(ethoxycarbonyl)oxirane

Downstream raw materials:

(2R)-1-[(4-Methylphenyl)sulfonyl]-2-[(2R)-oxiran-2-yl]aziridine

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

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

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