(-)-[(8S)-4-benzyloxy-3-benzyloxycarbonyl-2-methoxycarbonyl-8,9-dihydro-8-(methanesulfonyloxy)pyrrolo[3,2-f]quinolin-6(7H)-yl](5-benzyloxy-6-methoxy-1H-indol-2-yl)methanone

Base Information

Chemical Name:(-)-[(8S)-4-benzyloxy-3-benzyloxycarbonyl-2-methoxycarbonyl-8,9-dihydro-8-(methanesulfonyloxy)pyrrolo[3,2-f]quinolin-6(7H)-yl](5-benzyloxy-6-methoxy-1H-indol-2-yl)methanone
CAS No.:898530-81-9
Molecular Formula:C₄₆H₄₁N₃O₁₁S
Molecular Weight:843.911
Hs Code.:

(-)-[(8S)-4-benzyloxy-3-benzyloxycarbonyl-2-methoxycarbonyl-8,9-dihydro-8-(methanesulfonyloxy)pyrrolo[3,2-f]quinolin-6(7H)-yl](5-benzyloxy-6-methoxy-1H-indol-2-yl)methanone

Synonyms:(-)-[(8S)-4-benzyloxy-3-benzyloxycarbonyl-2-methoxycarbonyl-8,9-dihydro-8-(methanesulfonyloxy)pyrrolo[3,2-f]quinolin-6(7H)-yl](5-benzyloxy-6-methoxy-1H-indol-2-yl)methanone

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Chemical Property of (-)-[(8S)-4-benzyloxy-3-benzyloxycarbonyl-2-methoxycarbonyl-8,9-dihydro-8-(methanesulfonyloxy)pyrrolo[3,2-f]quinolin-6(7H)-yl](5-benzyloxy-6-methoxy-1H-indol-2-yl)methanone

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Technology Process of (-)-[(8S)-4-benzyloxy-3-benzyloxycarbonyl-2-methoxycarbonyl-8,9-dihydro-8-(methanesulfonyloxy)pyrrolo[3,2-f]quinolin-6(7H)-yl](5-benzyloxy-6-methoxy-1H-indol-2-yl)methanone

There total 22 articles about (-)-[(8S)-4-benzyloxy-3-benzyloxycarbonyl-2-methoxycarbonyl-8,9-dihydro-8-(methanesulfonyloxy)pyrrolo[3,2-f]quinolin-6(7H)-yl](5-benzyloxy-6-methoxy-1H-indol-2-yl)methanone 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: 1.64%

: 4-benzyloxy-6-(5-benzyloxy-6-methoxy-1H-indole-2-carbonyl)-8-hydroxy-6,7,8,9-tetrahydro-pyrrolo[3,2-f]quinoline-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester

: 124-63-0
methanesulfonyl chloride

: 898530-81-9
(-)-[(8S)-4-benzyloxy-3-benzyloxycarbonyl-2-methoxycarbonyl-8,9-dihydro-8-(methanesulfonyloxy)pyrrolo[3,2-f]quinolin-6(7H)-yl](5-benzyloxy-6-methoxy-1H-indol-2-yl)methanone

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/ja0619455

Reference yield:

: 898530-71-7
(-)-(2S)-3-azido-1-(4-benzyloxy-2,6-bromophenyl)propan-2-ol

: 898530-81-9
(-)-[(8S)-4-benzyloxy-3-benzyloxycarbonyl-2-methoxycarbonyl-8,9-dihydro-8-(methanesulfonyloxy)pyrrolo[3,2-f]quinolin-6(7H)-yl](5-benzyloxy-6-methoxy-1H-indol-2-yl)methanone

Guidance literature:: Multi-step reaction with 12 steps

1: 15.0 g / imidazole; DMAP / dimethylformamide / 6 h / 50 °C

2: tetrahydrofuran / 0.5 h / 20 °C

3: water / tetrahydrofuran / 2 h / 20 °C

4: 16.4 g / sodium bicarbonate / tetrahydrofuran; H₂O / 42 h / 20 °C

5: 83 percent / copper iodide; cesium acetate / dimethylsulfoxide / 24 h / 60 °C

6: 89 percent / lithium chloride; triethylamine / Pd₂(dba)3; 2-di(tert-butyl)phosphine-1,1'-diphenyl / dimethylformamide / 1 h / 90 °C

7: 99 percent / cesium carbonate; thiophenol / acetonitrile / 0.5 h / 20 °C

8: 90 percent / N-bromosuccinimide / CH₂Cl₂ / 0.33 h / 0 °C

9: 100 percent / copper iodide; cesium actate / dimethylsulfoxide / 12 h / 20 °C

10: 100 percent / pyridine / CH₂Cl₂ / 0.08 h / 0 °C

11: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

12: 1.64 percent / pyridine / CH₂Cl₂ / 4 h / 20 °C

With pyridine; 1H-imidazole; dmap; N-Bromosuccinimide; copper(l) iodide; tetrabutyl ammonium fluoride; water; cesium acetate; sodium hydrogencarbonate; caesium carbonate; thiophenol; triethylamine; lithium chloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; johnphos; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 2: Staudinger reaction / 6: Heck reaction;
DOI:10.1021/ja0619455

Reference yield:

: 898530-54-6
(-)-(2S)-1-(4-benzyloxy-2,6-dibromophenyl)-3-chloropropan-2-ol

: 898530-81-9
(-)-[(8S)-4-benzyloxy-3-benzyloxycarbonyl-2-methoxycarbonyl-8,9-dihydro-8-(methanesulfonyloxy)pyrrolo[3,2-f]quinolin-6(7H)-yl](5-benzyloxy-6-methoxy-1H-indol-2-yl)methanone

Guidance literature:: Multi-step reaction with 13 steps

1: 12.8 g / NaN₃ / dimethylformamide / 9 h / 90 °C

2: 15.0 g / imidazole; DMAP / dimethylformamide / 6 h / 50 °C

3: tetrahydrofuran / 0.5 h / 20 °C

4: water / tetrahydrofuran / 2 h / 20 °C

5: 16.4 g / sodium bicarbonate / tetrahydrofuran; H₂O / 42 h / 20 °C

6: 83 percent / copper iodide; cesium acetate / dimethylsulfoxide / 24 h / 60 °C

7: 89 percent / lithium chloride; triethylamine / Pd₂(dba)3; 2-di(tert-butyl)phosphine-1,1'-diphenyl / dimethylformamide / 1 h / 90 °C

8: 99 percent / cesium carbonate; thiophenol / acetonitrile / 0.5 h / 20 °C

9: 90 percent / N-bromosuccinimide / CH₂Cl₂ / 0.33 h / 0 °C

10: 100 percent / copper iodide; cesium actate / dimethylsulfoxide / 12 h / 20 °C

11: 100 percent / pyridine / CH₂Cl₂ / 0.08 h / 0 °C

12: tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

13: 1.64 percent / pyridine / CH₂Cl₂ / 4 h / 20 °C

With pyridine; 1H-imidazole; dmap; N-Bromosuccinimide; copper(l) iodide; sodium azide; tetrabutyl ammonium fluoride; water; cesium acetate; sodium hydrogencarbonate; caesium carbonate; thiophenol; triethylamine; lithium chloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; johnphos; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 3: Staudinger reaction / 7: Heck reaction;
DOI:10.1021/ja0619455