ethyl (4S)-4-benzyloxycarbonylamino-3-oxo-2-triphenylphosphoranylidenepentanoate

Base Information

• Chemical Name: ethyl (4S)-4-benzyloxycarbonylamino-3-oxo-2-triphenylphosphoranylidenepentanoate
• CAS No.: 166540-08-5
• Molecular Formula: C₃₃H₃₂NO₅P
• Molecular Weight: 553.595

Synonyms:ethyl (4S)-4-benzyloxycarbonylamino-3-oxo-2-triphenylphosphoranylidenepentanoate

Chemical Property of ethyl (4S)-4-benzyloxycarbonylamino-3-oxo-2-triphenylphosphoranylidenepentanoate

Chemical Property:

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Technology Process of ethyl (4S)-4-benzyloxycarbonylamino-3-oxo-2-triphenylphosphoranylidenepentanoate

There total 2 articles about ethyl (4S)-4-benzyloxycarbonylamino-3-oxo-2-triphenylphosphoranylidenepentanoate 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: 86.0%

ethyl (triphenylphosphoranylidene)acetate (1099-45-2) + benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate (820239-42-7) → ethyl (4S)-4-benzyloxycarbonylamino-3-oxo-2-triphenylphosphoranylidenepentanoate (166540-08-5)

Guidance literature:

In acetonitrile; at 60 ℃; for 0.166667h; Microwave irradiation;

DOI:10.3987/COM-08-S(F)12

Reference yield: 46.0%

N-Cbz-Ala (1142-20-7) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (4S)-4-benzyloxycarbonylamino-3-oxo-2-triphenylphosphoranylidenepentanoate (166540-08-5)

Guidance literature:

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

DOI:10.1039/CC9960002079

Reference yield: 99.0%

ethyl (4S)-4-benzyloxycarbonylamino-3-oxo-2-triphenylphosphoranylidenepentanoate (166540-08-5) → (4RS)-4-amino-1-ethoxy-2-(triphenylphosphonio)pentane-1,3-dione bromide hydrobromide (1105712-35-3)

Guidance literature:

With hydrogen bromide; In acetic acid; at 20 ℃; for 5h;

DOI:10.3987/COM-08-S(F)12

upstream raw materials:

N-Cbz-Ala

ethyl (triphenylphosphoranylidene)acetate

benzyl N-[(1S)-2-(1H-1,2,3-benzotriazol-1-yl)-1-methyl-2-oxoethyl]carbamate

Downstream raw materials:

ethyl (4S)-4-(benzyloxycarbonylamino)pent-2-ynoate

(3S)-3-(benzyloxycarbonylamino)but-1-yne

(4RS)-4-amino-1-ethoxy-2-(triphenylphosphonio)pentane-1,3-dione bromide hydrobromide

(5RS)-5-methyl-3-(triphenylphosphoranylidene)pyrrolidine-2,4-dione

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