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

Base Information

Chemical Name:2-(3-{4-benzyloxy-3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid tert-butyl ester
CAS No.:421556-74-3
Molecular Formula:C₅₇H₇₇N₅O₁₃Si
Molecular Weight:1068.35
Hs Code.:

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

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

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

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

There total 20 articles about 2-(3-{4-benzyloxy-3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-phenyl}-2-benzyloxycarbonylamino-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:

: 13154-24-0
triisopropylsilyl chloride

: 421556-73-2
2-(3-{4-benzyloxy-3-[3-(2-tert-butoxycarbonylamino-1,3-dihydroxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid tert-butyl ester

: 421556-74-3
2-(3-{4-benzyloxy-3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid tert-butyl ester

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1002/1521-3773(20020201)41:3<512::AID-ANIE512>3.0.CO;2-R

Reference yield:

: 31676-49-0
7-iodooxindole

: 421556-74-3
2-(3-{4-benzyloxy-3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: 45 percent / Et₃N; MsCl / CH₂Cl₂ / 1.33 h / -75 - -50 °C

2.1: 65 percent / K₂CO₃; [PdCl₂(dppf)]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 5 h / 80 °C

3.1: aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

4.1: 85 percent / 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 2.5 h / 20 °C

5.1: OsO₄; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / 2-methyl-propan-2-ol; H₂O / 14 h / 20 °C

6.1: pyridinum p-toluene sulfonate / methanol / 4 h / 70 °C

7.1: 287 mg / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 2.5 h / 20 °C

With 1H-imidazole; dmap; (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; pyridinium p-toluenesulfonate; potassium carbonate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; water; tert-butyl alcohol; 2.1: Suzuki coupling;
DOI:10.1021/ja049821k

Reference yield:

: 95715-87-0
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

: 421556-74-3
2-(3-{4-benzyloxy-3-[3-(2-tert-butoxycarbonylamino-1-hydroxy-3-triisopropylsilanyloxy-propyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-7-yl]-phenyl}-2-benzyloxycarbonylamino-propionylamino)-succinamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: 45 percent / Et₃N; MsCl / CH₂Cl₂ / 1.33 h / -75 - -50 °C

2.1: 65 percent / K₂CO₃; [PdCl₂(dppf)]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 5 h / 80 °C

3.1: aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

4.1: 85 percent / 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 2.5 h / 20 °C

5.1: OsO₄; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / 2-methyl-propan-2-ol; H₂O / 14 h / 20 °C

6.1: pyridinum p-toluene sulfonate / methanol / 4 h / 70 °C

7.1: 287 mg / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 2.5 h / 20 °C

With 1H-imidazole; dmap; (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; pyridinium p-toluenesulfonate; potassium carbonate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; water; tert-butyl alcohol; 2.1: Suzuki coupling;
DOI:10.1021/ja049821k