(2S,9S,9aR)-9-Hydroxy-2-methyl-9-((1S,4S)-1-methyl-3,10-dioxo-1,3,4,10-tetrahydro-2H-2,4a,9-triaza-anthracen-4-ylmethyl)-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,9S,9aR)-9-Hydroxy-2-methyl-9-((1S,4S)-1-methyl-3,10-dioxo-1,3,4,10-tetrahydro-2H-2,4a,9-triaza-anthracen-4-ylmethyl)-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester
• CAS No.: 316828-55-4
• Molecular Formula: C₃₂H₂₉N₅O₆
• Molecular Weight: 579.612

Synonyms:(2S,9S,9aR)-9-Hydroxy-2-methyl-9-((1S,4S)-1-methyl-3,10-dioxo-1,3,4,10-tetrahydro-2H-2,4a,9-triaza-anthracen-4-ylmethyl)-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

Chemical Property of (2S,9S,9aR)-9-Hydroxy-2-methyl-9-((1S,4S)-1-methyl-3,10-dioxo-1,3,4,10-tetrahydro-2H-2,4a,9-triaza-anthracen-4-ylmethyl)-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

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Technology Process of (2S,9S,9aR)-9-Hydroxy-2-methyl-9-((1S,4S)-1-methyl-3,10-dioxo-1,3,4,10-tetrahydro-2H-2,4a,9-triaza-anthracen-4-ylmethyl)-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester

There total 20 articles about (2S,9S,9aR)-9-Hydroxy-2-methyl-9-((1S,4S)-1-methyl-3,10-dioxo-1,3,4,10-tetrahydro-2H-2,4a,9-triaza-anthracen-4-ylmethyl)-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic 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: 65.0%

C37H40N6O6 → N-19-benzyloxycarbonyl-fumiquinazoline A (316828-53-2) + (2S,9S,9aR)-9-Hydroxy-2-methyl-9-((1S,4S)-1-methyl-3,10-dioxo-1,3,4,10-tetrahydro-2H-2,4a,9-triaza-anthracen-4-ylmethyl)-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester (316828-55-4)

Guidance literature:

In acetonitrile; for 2h; Heating;

DOI:10.1021/ol0067686

Reference yield:

N-Cbz-Ala (1142-20-7) → (2S,9S,9aR)-9-Hydroxy-2-methyl-9-((1S,4S)-1-methyl-3,10-dioxo-1,3,4,10-tetrahydro-2H-2,4a,9-triaza-anthracen-4-ylmethyl)-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester (316828-55-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: DCC / CH₂Cl₂ / 0.33 h / 20 °C

2.1: 3.53 g / DDQ / toluene / 2 h / 110 °C

3.1: Hg(OTFA)2 / CH₂Cl₂ / 0.33 h / 20 °C

3.2: 85 percent / I₂ / CH₂Cl₂ / 3 h / 20 °C

4.1: 64 percent / P(o-tolyl)3; K₂CO₃ / Pd₂(dba)3 / toluene / 2 h / 105 °C

5.1: 65 percent / 7b-Bu-7bH-oxaziridino[2,3-b][1,2]benzisothiazole-3,3-dioxide / CH₂Cl₂ / 12 h / 20 °C

6.1: 9 percent / NaBH₄; AcOH / 2 h / 25 °C

7.1: Zn dust; AcOH / 0.5 h / 20 °C

8.1: 134 mg / EDAC / acetonitrile / 1.33 h / 20 °C

9.1: 89 percent / EDAC / acetonitrile / 1.5 h / 20 °C

10.1: 76 percent / PPh₃; Br₂; Et₃N / CH₂Cl₂ / 0.25 h / 20 °C

11.1: ethyl acetate / 0.17 h / 20 °C

12.1: 11 mg / acetonitrile / 2 h / Heating

With sodium tetrahydroborate; 7b-Bu-7bH-oxaziridino[2,3-b][1,2]benzisothiazole-3,3-dioxide; bromine; mercury(II) trifluoroacetate; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; tris-(o-tolyl)phosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In dichloromethane; ethyl acetate; toluene; acetonitrile;

DOI:10.1021/jo0264980

Reference yield:

(R)-(+)-tryptophan methyl ester hydrochloride (14907-27-8,5619-09-0,7524-52-9,26988-71-6,41222-70-2,67557-19-1,109492-62-8) → (2S,9S,9aR)-9-Hydroxy-2-methyl-9-((1S,4S)-1-methyl-3,10-dioxo-1,3,4,10-tetrahydro-2H-2,4a,9-triaza-anthracen-4-ylmethyl)-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester (316828-55-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 96 percent / NaHCO₃ / diethyl ether; H₂O / 4 h / 20 °C

2.1: 92 percent / BH₃*THF / tetrahydrofuran; trifluoroacetic acid / 1 h / 0 °C

3.1: DCC / CH₂Cl₂ / 0.33 h / 20 °C

4.1: 3.53 g / DDQ / toluene / 2 h / 110 °C

5.1: Hg(OTFA)2 / CH₂Cl₂ / 0.33 h / 20 °C

5.2: 85 percent / I₂ / CH₂Cl₂ / 3 h / 20 °C

6.1: 64 percent / P(o-tolyl)3; K₂CO₃ / Pd₂(dba)3 / toluene / 2 h / 105 °C

7.1: 65 percent / 7b-Bu-7bH-oxaziridino[2,3-b][1,2]benzisothiazole-3,3-dioxide / CH₂Cl₂ / 12 h / 20 °C

8.1: 9 percent / NaBH₄; AcOH / 2 h / 25 °C

9.1: Zn dust; AcOH / 0.5 h / 20 °C

10.1: 134 mg / EDAC / acetonitrile / 1.33 h / 20 °C

11.1: 89 percent / EDAC / acetonitrile / 1.5 h / 20 °C

12.1: 76 percent / PPh₃; Br₂; Et₃N / CH₂Cl₂ / 0.25 h / 20 °C

13.1: ethyl acetate / 0.17 h / 20 °C

14.1: 11 mg / acetonitrile / 2 h / Heating

With sodium tetrahydroborate; borane-THF; 7b-Bu-7bH-oxaziridino[2,3-b][1,2]benzisothiazole-3,3-dioxide; bromine; mercury(II) trifluoroacetate; sodium hydrogencarbonate; potassium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; tris-(o-tolyl)phosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; toluene; acetonitrile; trifluoroacetic acid;

DOI:10.1021/jo0264980

upstream raw materials:

N-Cbz-Ala

(R)-(+)-tryptophan methyl ester hydrochloride

anthranilic acid

N_α-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester

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