ethyl (4S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-2-triphenylphosphoranylidenehexanoate

Base Information

• Chemical Name: ethyl (4S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-2-triphenylphosphoranylidenehexanoate
• CAS No.: 166540-09-6
• Molecular Formula: C₃₅H₃₆NO₅P
• Molecular Weight: 581.648

Synonyms:ethyl (4S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-2-triphenylphosphoranylidenehexanoate

Chemical Property of ethyl (4S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-2-triphenylphosphoranylidenehexanoate

Chemical Property:

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Technology Process of ethyl (4S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-2-triphenylphosphoranylidenehexanoate

There total 2 articles about ethyl (4S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-2-triphenylphosphoranylidenehexanoate 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: 49.0%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (4S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-2-triphenylphosphoranylidenehexanoate (166540-09-6)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;

DOI:10.1039/CC9960002079

Reference yield:

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) → ethyl (4S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-2-triphenylphosphoranylidenehexanoate (166540-09-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 58 percent / aq. NaOH / 3 h / 0 °C

2: 49 percent / EDCI; DMAP / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; sodium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane;

DOI:10.1039/b110243e

Reference yield: 89.0%

ethyl (4S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-2-triphenylphosphoranylidenehexanoate (166540-09-6) → (S)-4-Amino-5-methyl-3-oxo-2-(triphenyl-λ5-phosphanylidene)-hexanoic acid ethyl ester

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/S0040-4039(00)01905-5

upstream raw materials:

(S)-N-(benzyloxycarbonyl)valine

ethyl (triphenylphosphoranylidene)acetate

L-valine

Downstream raw materials:

ethyl (4S)-4-benzyloxycarbonylamino-5-methylhex-2-ynoate

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