(S)-2-Benzyloxycarbonylamino-3-{5'-[(S)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-2-methoxycarbonyl-ethyl]-6,2'-dihydroxy-biphenyl-3-yl}-propionic acid 4-nitro-phenyl ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-3-{5'-[(S)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-2-methoxycarbonyl-ethyl]-6,2'-dihydroxy-biphenyl-3-yl}-propionic acid 4-nitro-phenyl ester
• CAS No.: 132149-68-9
• Molecular Formula: C₄₁H₄₄N₄O₁₃
• Molecular Weight: 800.819

Synonyms:(S)-2-Benzyloxycarbonylamino-3-{5'-[(S)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-2-methoxycarbonyl-ethyl]-6,2'-dihydroxy-biphenyl-3-yl}-propionic acid 4-nitro-phenyl ester

Chemical Property of (S)-2-Benzyloxycarbonylamino-3-{5'-[(S)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-2-methoxycarbonyl-ethyl]-6,2'-dihydroxy-biphenyl-3-yl}-propionic acid 4-nitro-phenyl ester

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Technology Process of (S)-2-Benzyloxycarbonylamino-3-{5'-[(S)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-2-methoxycarbonyl-ethyl]-6,2'-dihydroxy-biphenyl-3-yl}-propionic acid 4-nitro-phenyl ester

There total 3 articles about (S)-2-Benzyloxycarbonylamino-3-{5'-[(S)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-2-methoxycarbonyl-ethyl]-6,2'-dihydroxy-biphenyl-3-yl}-propionic acid 4-nitro-phenyl 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: 9.0%

4-nitrophenyl N-[(benzyloxy)carbonyl]-L-tyrosinate (3556-56-7) + L-N-Boc-Ala-L-Tyr methyl ester (84794-40-1) → (S)-2-Benzyloxycarbonylamino-3-{5'-[(S)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-2-methoxycarbonyl-ethyl]-6,2'-dihydroxy-biphenyl-3-yl}-propionic acid 4-nitro-phenyl ester (132149-68-9) + (S)-2-Benzyloxycarbonylamino-3-{5'-[(S)-2-benzyloxycarbonylamino-2-(4-nitro-phenoxycarbonyl)-ethyl]-6,2'-dihydroxy-biphenyl-3-yl}-propionic acid 4-nitro-phenyl ester (132149-67-8)

Guidance literature:

With vanadium(V) oxychloride; In tetrahydrofuran; for 2h; -60 deg C -> 0 deg C;

DOI:10.1016/S0040-4039(00)97122-3

Reference yield:

L-N-Boc-Ala (15761-38-3) → (S)-2-Benzyloxycarbonylamino-3-{5'-[(S)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-2-methoxycarbonyl-ethyl]-6,2'-dihydroxy-biphenyl-3-yl}-propionic acid 4-nitro-phenyl ester (132149-68-9)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC, HOBT / tetrahydrofuran; dimethylformamide

2: 7 percent / VOCl₃ / tetrahydrofuran / 2 h / -60 deg C -> 0 deg C

With vanadium(V) oxychloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97122-3

Reference yield:

L-Tyr-OMe (1080-06-4) → (S)-2-Benzyloxycarbonylamino-3-{5'-[(S)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-2-methoxycarbonyl-ethyl]-6,2'-dihydroxy-biphenyl-3-yl}-propionic acid 4-nitro-phenyl ester (132149-68-9)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC, HOBT / tetrahydrofuran; dimethylformamide

2: 7 percent / VOCl₃ / tetrahydrofuran / 2 h / -60 deg C -> 0 deg C

With vanadium(V) oxychloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97122-3

upstream raw materials:

4-nitrophenyl N-[(benzyloxy)carbonyl]-L-tyrosinate

L-N-Boc-Ala-L-Tyr methyl ester

L-N-Boc-Ala

L-Tyr-OMe

Downstream raw materials:

(8S,11S,14S)-14-Benzyloxycarbonylamino-3,19-dihydroxy-11-methyl-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carboxylic acid methyl ester

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