ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-4-tert-butyldiphenylsiloxy-2-pentenoate

Base Information

• Chemical Name: ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-4-tert-butyldiphenylsiloxy-2-pentenoate
• CAS No.: 502442-58-2
• Molecular Formula: C₃₄H₅₃NO₆Si₂
• Molecular Weight: 627.969

Synonyms:ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-4-tert-butyldiphenylsiloxy-2-pentenoate

Chemical Property of ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-4-tert-butyldiphenylsiloxy-2-pentenoate

Chemical Property:

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Technology Process of ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-4-tert-butyldiphenylsiloxy-2-pentenoate

There total 4 articles about ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-4-tert-butyldiphenylsiloxy-2-pentenoate 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: 100.0%

tert-butylchlorodiphenylsilane (58479-61-1) + ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-2-pentenoate (502442-56-0) → ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-4-tert-butyldiphenylsiloxy-2-pentenoate (502442-58-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1246/bcsj.75.2517

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-4-tert-butyldiphenylsiloxy-2-pentenoate (502442-58-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / DMAP; TEA / CH₂Cl₂ / 20 °C

2: 100 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; dmap; TEA; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.75.2517

Reference yield:

ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-4,5-dihydroxy-2-pentenoate (502442-53-7) → ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-4-tert-butyldiphenylsiloxy-2-pentenoate (502442-58-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / DMAP; TEA / CH₂Cl₂ / 20 °C

2: 100 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; dmap; TEA; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.75.2517

upstream raw materials:

tert-butylchlorodiphenylsilane

ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-5-tert-butyldimethylsiloxy-2-pentenoate

tert-butyldimethylsilyl chloride

ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-4,5-dihydroxy-2-pentenoate

Downstream raw materials:

ethyl (2S,4S)-N-tert-butyloxycarbonyl-4-tert-butyldiphenylsiloxyprolinate

ethyl (4S)-N-tert-butyloxycarbonyl-4-tert-butyldiphenylsiloxy-α,β-didehydroprolinate

N-tert-butoxycarbonyl-L-cis-4-hydroxyproline

ethyl (4S)-2-(N-tert-butyloxycarbonylamino)-4-tert-butyldiphenylsiloxy-5-hydroxy-2-pentenoate

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