(-)-methyl 3-[(8S)-4-benzyloxy-6-(5-benzyloxy-6-methoxy-1H-indol-2-yl)carbonyl-6,7,8,9-tetrahydro-8-methanesulfonyloxy-3H-pyrrolo[3,2-f]quinoline-2-yl]carbonyl-4-hydroxy-5-methoxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-thiocarboxylate

Base Information

Chemical Name:(-)-methyl 3-[(8S)-4-benzyloxy-6-(5-benzyloxy-6-methoxy-1H-indol-2-yl)carbonyl-6,7,8,9-tetrahydro-8-methanesulfonyloxy-3H-pyrrolo[3,2-f]quinoline-2-yl]carbonyl-4-hydroxy-5-methoxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-thiocarboxylate
CAS No.:898530-69-3
Molecular Formula:C₅₀H₄₅N₅O₁₁S₂
Molecular Weight:956.066
Hs Code.:

(-)-methyl 3-[(8S)-4-benzyloxy-6-(5-benzyloxy-6-methoxy-1H-indol-2-yl)carbonyl-6,7,8,9-tetrahydro-8-methanesulfonyloxy-3H-pyrrolo[3,2-f]quinoline-2-yl]carbonyl-4-hydroxy-5-methoxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-thiocarboxylate

Synonyms:(-)-methyl 3-[(8S)-4-benzyloxy-6-(5-benzyloxy-6-methoxy-1H-indol-2-yl)carbonyl-6,7,8,9-tetrahydro-8-methanesulfonyloxy-3H-pyrrolo[3,2-f]quinoline-2-yl]carbonyl-4-hydroxy-5-methoxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-thiocarboxylate

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Chemical Property of (-)-methyl 3-[(8S)-4-benzyloxy-6-(5-benzyloxy-6-methoxy-1H-indol-2-yl)carbonyl-6,7,8,9-tetrahydro-8-methanesulfonyloxy-3H-pyrrolo[3,2-f]quinoline-2-yl]carbonyl-4-hydroxy-5-methoxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-thiocarboxylate

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Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (-)-methyl 3-[(8S)-4-benzyloxy-6-(5-benzyloxy-6-methoxy-1H-indol-2-yl)carbonyl-6,7,8,9-tetrahydro-8-methanesulfonyloxy-3H-pyrrolo[3,2-f]quinoline-2-yl]carbonyl-4-hydroxy-5-methoxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-thiocarboxylate

There total 42 articles about (-)-methyl 3-[(8S)-4-benzyloxy-6-(5-benzyloxy-6-methoxy-1H-indol-2-yl)carbonyl-6,7,8,9-tetrahydro-8-methanesulfonyloxy-3H-pyrrolo[3,2-f]quinoline-2-yl]carbonyl-4-hydroxy-5-methoxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-thiocarboxylate 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:

: 898530-59-1
5,8-dibromo-3,4-dihydro-6,7-dimethoxyisoquinoline

: 898530-69-3
(-)-methyl 3-[(8S)-4-benzyloxy-6-(5-benzyloxy-6-methoxy-1H-indol-2-yl)carbonyl-6,7,8,9-tetrahydro-8-methanesulfonyloxy-3H-pyrrolo[3,2-f]quinoline-2-yl]carbonyl-4-hydroxy-5-methoxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-thiocarboxylate

Guidance literature:: Multi-step reaction with 14 steps

1: tetrahydrofuran / 1.08 h / 0 - 20 °C

2: aq. sodium bicarbonate / tetrahydrofuran / 0.5 h / 20 °C

3: 425.5 mg / sodium borohydride / methanol / 1 h / 0 - 20 °C

4: copper iodide; cesium acetate / dimethylsulfoxide / 24 h / 80 °C

5: 9.75 g / 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / 20 °C

6: 84 percent / 1,1,3,3-tetramethylguanidine / CH₂Cl₂ / 6 h / 20 °C

7: 77 percent / copper iodide; cesium acetate / dimethylsulfoxide / 12 h / 20 °C

8: 95 percent / cesium carbonate; thiophenol / acetonitrile / 3 h / 20 °C

9: 91 percent / NaHCO₃ / tetrahydrofuran; H₂O / 0.17 h / 20 °C

10: hydrogen / Pd/C / ethanol; tetrahydrofuran / 3 h / 20 °C / 760 Torr

11: 1.11 g / water-soluble carbodiimide hydrochloride; DMAP / dimethylformamide / 3 h / 0 °C

12: 97 percent / BCl₃ / CH₂Cl₂ / 0.33 h / 0 °C

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

14: 1.15 g / 1-hydroxybenzotriazole hydrate; water-soluble carbodiimide hydrochloride / tetrahydrofuran / 2 h / 20 °C

With dmap; sodium tetrahydroborate; copper(l) iodide; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; cesium acetate; boron trichloride; sodium hydrogencarbonate; caesium carbonate; thiophenol; 4-methylmorpholine N-oxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N,N',N'-tetramethylguanidine; palladium on activated charcoal; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 6: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ja0619455

Reference yield:

: 898530-75-1
5,8-dibromo-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline

: 898530-69-3
(-)-methyl 3-[(8S)-4-benzyloxy-6-(5-benzyloxy-6-methoxy-1H-indol-2-yl)carbonyl-6,7,8,9-tetrahydro-8-methanesulfonyloxy-3H-pyrrolo[3,2-f]quinoline-2-yl]carbonyl-4-hydroxy-5-methoxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-thiocarboxylate

Guidance literature:: Multi-step reaction with 15 steps

1: 18.16 g / manganese oxide / CH₂Cl₂ / 18 h / 20 °C

2: tetrahydrofuran / 1.08 h / 0 - 20 °C

3: aq. sodium bicarbonate / tetrahydrofuran / 0.5 h / 20 °C

4: 425.5 mg / sodium borohydride / methanol / 1 h / 0 - 20 °C

5: copper iodide; cesium acetate / dimethylsulfoxide / 24 h / 80 °C

6: 9.75 g / 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / 20 °C

7: 84 percent / 1,1,3,3-tetramethylguanidine / CH₂Cl₂ / 6 h / 20 °C

8: 77 percent / copper iodide; cesium acetate / dimethylsulfoxide / 12 h / 20 °C

9: 95 percent / cesium carbonate; thiophenol / acetonitrile / 3 h / 20 °C

10: 91 percent / NaHCO₃ / tetrahydrofuran; H₂O / 0.17 h / 20 °C

11: hydrogen / Pd/C / ethanol; tetrahydrofuran / 3 h / 20 °C / 760 Torr

12: 1.11 g / water-soluble carbodiimide hydrochloride; DMAP / dimethylformamide / 3 h / 0 °C

13: 97 percent / BCl₃ / CH₂Cl₂ / 0.33 h / 0 °C

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

15: 1.15 g / 1-hydroxybenzotriazole hydrate; water-soluble carbodiimide hydrochloride / tetrahydrofuran / 2 h / 20 °C

With dmap; manganese oxide; sodium tetrahydroborate; copper(l) iodide; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; cesium acetate; boron trichloride; sodium hydrogencarbonate; caesium carbonate; thiophenol; 4-methylmorpholine N-oxide; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N,N',N'-tetramethylguanidine; palladium on activated charcoal; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 7: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ja0619455

Reference yield:

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

: 898530-69-3
(-)-methyl 3-[(8S)-4-benzyloxy-6-(5-benzyloxy-6-methoxy-1H-indol-2-yl)carbonyl-6,7,8,9-tetrahydro-8-methanesulfonyloxy-3H-pyrrolo[3,2-f]quinoline-2-yl]carbonyl-4-hydroxy-5-methoxy-1,2-dihydro-3H-pyrrolo[3,2-e]indole-7-thiocarboxylate

Guidance literature:: Multi-step reaction with 14 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

13: 92 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 18 h / 20 °C

14: 1.15 g / 1-hydroxybenzotriazole hydrate; water-soluble carbodiimide hydrochloride / tetrahydrofuran / 2 h / 20 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; N-Bromosuccinimide; copper(l) iodide; tetrabutyl ammonium fluoride; water; cesium acetate; sodium hydrogencarbonate; caesium carbonate; thiophenol; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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