(14R,14aR)-13-tert-butyl-14-methyl-1,2,3,5,6,7,8,14,14a-nonahydro-3-oxo-2-hydroxy-6-(2-nitrobenzenesulfonyl)benzo[7,8]azonino[5,4-b]indole-13,14(1H)-dicarboxylate

Base Information

Chemical Name:(14R,14aR)-13-tert-butyl-14-methyl-1,2,3,5,6,7,8,14,14a-nonahydro-3-oxo-2-hydroxy-6-(2-nitrobenzenesulfonyl)benzo[7,8]azonino[5,4-b]indole-13,14(1H)-dicarboxylate
CAS No.:762252-32-4
Molecular Formula:C₃₁H₃₃N₃O₁₀S
Molecular Weight:639.683
Hs Code.:

(14R,14aR)-13-tert-butyl-14-methyl-1,2,3,5,6,7,8,14,14a-nonahydro-3-oxo-2-hydroxy-6-(2-nitrobenzenesulfonyl)benzo[7,8]azonino[5,4-b]indole-13,14(1H)-dicarboxylate

Synonyms:(14R,14aR)-13-tert-butyl-14-methyl-1,2,3,5,6,7,8,14,14a-nonahydro-3-oxo-2-hydroxy-6-(2-nitrobenzenesulfonyl)benzo[7,8]azonino[5,4-b]indole-13,14(1H)-dicarboxylate

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Chemical Property of (14R,14aR)-13-tert-butyl-14-methyl-1,2,3,5,6,7,8,14,14a-nonahydro-3-oxo-2-hydroxy-6-(2-nitrobenzenesulfonyl)benzo[7,8]azonino[5,4-b]indole-13,14(1H)-dicarboxylate

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Technology Process of (14R,14aR)-13-tert-butyl-14-methyl-1,2,3,5,6,7,8,14,14a-nonahydro-3-oxo-2-hydroxy-6-(2-nitrobenzenesulfonyl)benzo[7,8]azonino[5,4-b]indole-13,14(1H)-dicarboxylate

There total 13 articles about (14R,14aR)-13-tert-butyl-14-methyl-1,2,3,5,6,7,8,14,14a-nonahydro-3-oxo-2-hydroxy-6-(2-nitrobenzenesulfonyl)benzo[7,8]azonino[5,4-b]indole-13,14(1H)-dicarboxylate 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:

: C₃₄H₄₁N₃O₉SSi

: 762252-32-4
(14R,14aR)-13-tert-butyl-14-methyl-1,2,3,5,6,7,8,14,14a-nonahydro-3-oxo-2-hydroxy-6-(2-nitrobenzenesulfonyl)benzo[7,8]azonino[5,4-b]indole-13,14(1H)-dicarboxylate

Guidance literature:: C₃₄H₄₁N₃O₉SSi; With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃;

With hydrogenchloride; In methanol; dichloromethane; at 0 ℃; for 0.0833333h;
DOI:10.1021/ja046407b

Reference yield:

: 5455-59-4
2-Nitrobenzenesulfonamide

: 762252-32-4
(14R,14aR)-13-tert-butyl-14-methyl-1,2,3,5,6,7,8,14,14a-nonahydro-3-oxo-2-hydroxy-6-(2-nitrobenzenesulfonyl)benzo[7,8]azonino[5,4-b]indole-13,14(1H)-dicarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: PPh₃; DEAD / toluene / 0.08 h / 20 °C

2.1: DBU / toluene / 3 h / 100 °C

2.2: aq. HCl / tetrahydrofuran / 2.5 h / 50 °C

2.3: 69 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

3.1: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

4.1: aq. NaHCO₃; mCPBA / CH₂Cl₂ / 0 °C

4.2: 270 mg / aq. HCl / CH₂Cl₂; methanol / 0.08 h / 0 °C

With sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In dichloromethane; toluene;
DOI:10.1021/ja046407b

Reference yield:

: 224315-42-8
2-[(1Z)-3-hydroxy-1-propenyl]phenylisothiocyanate

: 762252-32-4
(14R,14aR)-13-tert-butyl-14-methyl-1,2,3,5,6,7,8,14,14a-nonahydro-3-oxo-2-hydroxy-6-(2-nitrobenzenesulfonyl)benzo[7,8]azonino[5,4-b]indole-13,14(1H)-dicarboxylate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 98 percent / imidazole / CH₂Cl₂ / 0.08 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.17 h / 0 °C

2.2: 71 percent / NaH / tetrahydrofuran / 0 - 20 °C

3.1: 52 percent / Bu₃SnH; Et₃B / toluene; hexane / 0.17 h / 20 °C

4.1: 86 percent / Pd₂(dba)3; P(2-furyl)3 / toluene / 0.33 h / 20 °C

5.1: i-Pr₂NEt / CH₂Cl₂ / 3 h / 20 °C

6.1: LiI / 2,4,6-trimethyl-pyridine / 1 h / 80 °C

7.1: DMAP / acetonitrile / 0.33 h / 20 °C

8.1: NH₄F*HF / dimethylformamide; 1-methyl-pyrrolidin-2-one / 19 h / 20 °C

9.1: PPh₃; DEAD / toluene / 0.08 h / 20 °C

10.1: DBU / toluene / 3 h / 100 °C

10.2: aq. HCl / tetrahydrofuran / 2.5 h / 50 °C

10.3: 69 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

11.1: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

12.1: aq. NaHCO₃; mCPBA / CH₂Cl₂ / 0 °C

12.2: 270 mg / aq. HCl / CH₂Cl₂; methanol / 0.08 h / 0 °C

With 1H-imidazole; dmap; ammonium fluoride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifuran-2-yl-phosphane; triethyl borane; hydrogen fluoride; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium iodide; diethylazodicarboxylate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; 2,4,6-trimethyl-pyridine; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ja046407b