2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

Base Information

• Chemical Name: 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester
• CAS No.: 353520-92-0
• Molecular Formula: C₅₁H₇₃N₅O₁₃Si
• Molecular Weight: 992.252
• Mol file: 353520-92-0.mol

Synonyms:2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

Chemical Property of 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

There total 24 articles about 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl 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:

L-Tyr-OMe (1080-06-4) → 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester (353520-92-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / Na₂CO₃ / acetone; H₂O / 2 h / 20 °C

2: 86 percent / LiOH

3: 93 percent / I₂; Ag₂SO₄ / methanol / 1.5 h / 20 °C

4: 95 percent / [PdCl₂(dppf)]*CH₂Cl₂; KOAc / dimethylsulfoxide / 13 h / 80 °C

5: [PdCl₂(dppf)]*CH₂Cl₂; KOAc / 1,2-dimethoxy-ethane / 2 h / 80 °C

6: LiOH / tetrahydrofuran; H₂O / 1.5 h / 0 °C

7: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 2 h / 20 °C

8: OsO₄; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; lithium hydroxide; osmium(VIII) oxide; 1-hydroxy-7-aza-benzotriazole; iodine; potassium acetate; sodium carbonate; silver sulfate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; 4: Miyaura reaction / 5: Suzuki-Miyaura reaction;

DOI:10.1021/ja049821k

Reference yield:

N-(benzyloxycarbonyl)-L-tyrosine methyl ester (13512-31-7) → 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester (353520-92-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / LiOH

2: 93 percent / I₂; Ag₂SO₄ / methanol / 1.5 h / 20 °C

3: 95 percent / [PdCl₂(dppf)]*CH₂Cl₂; KOAc / dimethylsulfoxide / 13 h / 80 °C

4: [PdCl₂(dppf)]*CH₂Cl₂; KOAc / 1,2-dimethoxy-ethane / 2 h / 80 °C

5: LiOH / tetrahydrofuran; H₂O / 1.5 h / 0 °C

6: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 2 h / 20 °C

7: OsO₄; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; lithium hydroxide; osmium(VIII) oxide; 1-hydroxy-7-aza-benzotriazole; iodine; potassium acetate; silver sulfate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; dimethyl sulfoxide; tert-butyl alcohol; 3: Miyaura reaction / 4: Suzuki-Miyaura reaction;

DOI:10.1021/ja049821k

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → 2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester (353520-92-0)

Guidance literature:

Multi-step reaction with 9 steps

1: thionyl chloride / 21 h / -15 - 20 °C

2: 100 percent / Na₂CO₃ / acetone; H₂O / 2 h / 20 °C

3: 86 percent / LiOH

4: 93 percent / I₂; Ag₂SO₄ / methanol / 1.5 h / 20 °C

5: 95 percent / [PdCl₂(dppf)]*CH₂Cl₂; KOAc / dimethylsulfoxide / 13 h / 80 °C

6: [PdCl₂(dppf)]*CH₂Cl₂; KOAc / 1,2-dimethoxy-ethane / 2 h / 80 °C

7: LiOH / tetrahydrofuran; H₂O / 1.5 h / 0 °C

8: 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 2 h / 20 °C

9: OsO₄; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; lithium hydroxide; osmium(VIII) oxide; thionyl chloride; 1-hydroxy-7-aza-benzotriazole; iodine; potassium acetate; sodium carbonate; silver sulfate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; 5: Miyaura reaction / 6: Suzuki-Miyaura reaction;

DOI:10.1021/ja049821k

upstream raw materials:

triisopropylsilyl chloride

2-(2-benzyloxycarbonylamino-3-{3-[3-(2-tert-butoxycarbonylamino-3-triisopropylsilanyloxy-propylidene)-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-propionylamino)-succinamic acid tert-butyl ester

L-Tyr-OMe

L-asparagine tert-butyl ester

Downstream raw materials:

(S)-2-((S)-3-{3-[(S)-3-((1R,2R)-2-Amino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-4-methoxy-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid