(S)-3-{2'-Benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-5-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-6-hydroxy-biphenyl-3-yl}-2-benzyloxycarbonylamino-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-3-{2'-Benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-5-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-6-hydroxy-biphenyl-3-yl}-2-benzyloxycarbonylamino-propionic acid benzyl ester
• CAS No.: 866115-07-3
• Molecular Formula: C₇₉H₇₁N₃O₁₅
• Molecular Weight: 1302.44

Synonyms:(S)-3-{2'-Benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-5-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-6-hydroxy-biphenyl-3-yl}-2-benzyloxycarbonylamino-propionic acid benzyl ester

Chemical Property of (S)-3-{2'-Benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-5-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-6-hydroxy-biphenyl-3-yl}-2-benzyloxycarbonylamino-propionic acid benzyl ester

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Technology Process of (S)-3-{2'-Benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-5-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-6-hydroxy-biphenyl-3-yl}-2-benzyloxycarbonylamino-propionic acid benzyl ester

There total 19 articles about (S)-3-{2'-Benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-5-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-6-hydroxy-biphenyl-3-yl}-2-benzyloxycarbonylamino-propionic acid benzyl 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: 32.0%

(S)-2-Benzyloxycarbonylamino-3-{3-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-5-bromo-4-hydroxy-phenyl}-propionic acid benzyl ester (866115-06-2) + C31H28BF3NO5(1-)*K(1+) → (S)-3-{2'-Benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-5-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-6-hydroxy-biphenyl-3-yl}-2-benzyloxycarbonylamino-propionic acid benzyl ester (866115-07-3)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine; In water; isopropyl alcohol; for 48h; Heating;

DOI:10.1021/jo051076m

Reference yield:

(S)-2-Benzyloxycarbonylamino-3-[3-iodo-4-(4-methoxy-benzyloxy)-phenyl]-propionic acid benzyl ester (866114-99-0) → (S)-3-{2'-Benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-5-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-6-hydroxy-biphenyl-3-yl}-2-benzyloxycarbonylamino-propionic acid benzyl ester (866115-07-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Pd(dppf)Cl₂*CH₂Cl₂; KOAc; bis(neopentylglycolato)diboron / dimethylsulfoxide / 6 h / 80 °C

1.2: 89 percent / H₂O / ethyl acetate / 20 h / 20 °C

2.1: 81 percent / aq. H₂O₂ / methanol / 0.5 h / 20 °C

3.1: 80 percent / Cu(OAc)2; pyridine / CH₂Cl₂ / 48 h / 20 °C

4.1: 78 percent / DDQ / CH₂Cl₂; H₂O / 24 h / Heating

5.1: 70 percent / N-bromosuccinimide / dimethylformamide / 19 h / 80 °C

6.1: 32 percent / Et₃N; Pd(dppf)Cl₂*CH₂Cl₂ / propan-2-ol; H₂O / 48 h / Heating

With pyridine; N-Bromosuccinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; copper diacetate; dihydrogen peroxide; potassium acetate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane; In methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jo051076m

Reference yield:

benzyl N-carbobenzyloxy-L-tyrosine (5513-40-6) → (S)-3-{2'-Benzyloxy-5'-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-5-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-6-hydroxy-biphenyl-3-yl}-2-benzyloxycarbonylamino-propionic acid benzyl ester (866115-07-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 43 percent / silver sulfate; iodine / methanol / 5 h / 20 °C

2.1: K₂CO₃; tetrabutylammonium iodide / acetone / 0.5 h / 20 °C

2.2: 76 percent / acetone / 24 h / Heating

3.1: Pd(dppf)Cl₂*CH₂Cl₂; KOAc; bis(neopentylglycolato)diboron / dimethylsulfoxide / 6 h / 80 °C

3.2: 89 percent / H₂O / ethyl acetate / 20 h / 20 °C

4.1: 81 percent / aq. H₂O₂ / methanol / 0.5 h / 20 °C

5.1: 80 percent / Cu(OAc)2; pyridine / CH₂Cl₂ / 48 h / 20 °C

6.1: 78 percent / DDQ / CH₂Cl₂; H₂O / 24 h / Heating

7.1: 70 percent / N-bromosuccinimide / dimethylformamide / 19 h / 80 °C

8.1: 32 percent / Et₃N; Pd(dppf)Cl₂*CH₂Cl₂ / propan-2-ol; H₂O / 48 h / Heating

With pyridine; N-Bromosuccinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; copper diacetate; dihydrogen peroxide; iodine; potassium acetate; tetra-(n-butyl)ammonium iodide; potassium carbonate; silver sulfate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane; In methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; acetone;

DOI:10.1021/jo051076m

upstream raw materials:

(S)-2-Benzyloxycarbonylamino-3-{3-[4-((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-phenoxy]-5-bromo-4-hydroxy-phenyl}-propionic acid benzyl ester

(S)-2-Benzyloxycarbonylamino-3-[4-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-phenyl]-propionic acid benzyl ester

(S)-2-Benzyloxycarbonylamino-3-[3-hydroxy-4-(4-methoxy-benzyloxy)-phenyl]-propionic acid benzyl ester

(S)-2-Benzyloxycarbonylamino-3-[3-iodo-4-(4-methoxy-benzyloxy)-phenyl]-propionic acid benzyl ester

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