3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid ethyl ester

Base Information

• Chemical Name: 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid ethyl ester
• CAS No.: 185553-40-6
• Molecular Formula: C₄₇H₄₂NO₇P
• Molecular Weight: 763.827

Synonyms:3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid ethyl ester

Chemical Property of 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid ethyl ester

Chemical Property:

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Technology Process of 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid ethyl ester

There total 5 articles about 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid ethyl ester 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: 83.0%

ethyl (triphenylphosphoranylidene)acetate (1099-45-2) + (S)-2-Benzyloxycarbonylamino-3-(4-chlorocarbonyl-phenyl)-propionic acid benzyl ester → 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionic acid ethyl ester (185553-40-6)

Guidance literature:

With benzenesulfonamide; In toluene;

DOI:10.1016/0040-4039(96)01978-8

Reference yield:

benzyl N-carbobenzyloxy-L-tyrosine (5513-40-6) → 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionic acid ethyl ester (185553-40-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / Et₃N / CH₂Cl₂

2: 91 percent / Pd(OAc)2, (Ph₂PCH₂)2CH₂, Et₃N

3: 75 percent / 1M n-Bu₄NF, 4 Angstroem mol. sieves / tetrahydrofuran

4: (COCl)2, DMF / toluene

5: 83 percent / BSA / toluene

With benzenesulfonamide; palladium diacetate; oxalyl dichloride; 4 A molecular sieve; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/0040-4039(96)01978-8

Reference yield:

4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester (185553-34-8) → 3-[4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenyl]-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionic acid ethyl ester (185553-40-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / 1M n-Bu₄NF, 4 Angstroem mol. sieves / tetrahydrofuran

2: (COCl)2, DMF / toluene

3: 83 percent / BSA / toluene

With benzenesulfonamide; oxalyl dichloride; 4 A molecular sieve; tetrabutyl ammonium fluoride; N,N-dimethyl-formamide; In tetrahydrofuran; toluene;

DOI:10.1016/0040-4039(96)01978-8

upstream raw materials:

ethyl (triphenylphosphoranylidene)acetate

benzyl N-carbobenzyloxy-L-tyrosine

4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-benzoic acid 2-trimethylsilanyl-ethyl ester

4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-benzoic acid

Downstream raw materials:

3-{4-[(S)-2-Carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-phenyl}-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-propionic acid ethyl ester

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