(3aR,4S,5S,11bS)-methyl 3-benzyloxycarbonyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-cyclopropano-6-carboxylate

Base Information

Chemical Name:(3aR,4S,5S,11bS)-methyl 3-benzyloxycarbonyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-cyclopropano-6-carboxylate
CAS No.:362517-13-3
Molecular Formula:C₃₃H₃₈N₂O₆
Molecular Weight:558.675
Hs Code.:

(3aR,4S,5S,11bS)-methyl 3-benzyloxycarbonyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-cyclopropano-6-carboxylate

Synonyms:(3aR,4S,5S,11bS)-methyl 3-benzyloxycarbonyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-cyclopropano-6-carboxylate

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Chemical Property of (3aR,4S,5S,11bS)-methyl 3-benzyloxycarbonyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-cyclopropano-6-carboxylate

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Technology Process of (3aR,4S,5S,11bS)-methyl 3-benzyloxycarbonyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-cyclopropano-6-carboxylate

There total 8 articles about (3aR,4S,5S,11bS)-methyl 3-benzyloxycarbonyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-cyclopropano-6-carboxylate 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: 92.3%

: 362517-12-2
(3aR,4S,5S,11bS)-methyl 3-(benzyloxycarbonyl)-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5-hydroxymethyl-6-carboxylate

: 362517-13-3
(3aR,4S,5S,11bS)-methyl 3-benzyloxycarbonyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-cyclopropano-6-carboxylate

Guidance literature:: (3aR,4S,5S,11bS)-methyl 3-(benzyloxycarbonyl)-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5-hydroxymethyl-6-carboxylate; With dmap; p-toluenesulfonylanhydride; triethylamine; In dichloromethane; for 5h;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 24h; Further stages.;
DOI:10.1021/jo000250y

Reference yield:

: 362517-09-7
(3aR,4S,5S,11bS)-dimethyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-dicarboxylate

: 362517-13-3
(3aR,4S,5S,11bS)-methyl 3-benzyloxycarbonyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-cyclopropano-6-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 81.7 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0 - 20 °C

2.1: ammonium formate / Pd/C / methanol; ethyl acetate / 2 h / Heating

3.1: 6.940 g / sodium hydrogencarbonate / acetone; H₂O / 0.33 h / 0 °C

4.1: p-toluenesulfonic anhydride; triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 5 h

4.2: 92.3 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 24 h

With dmap; p-toluenesulfonylanhydride; ammonium formate; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; acetone;
DOI:10.1021/jo000250y

Reference yield:

: 362517-06-4
(3aR,4S,5S,11bS)-dimethyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-[(2R)-2-ethyl-2,3-epoxypropyl]-1H-pyrrolo[2,3-d]carbazole-5,6-dicarboxylate

: 362517-13-3
(3aR,4S,5S,11bS)-methyl 3-benzyloxycarbonyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-(isopropylidenedioxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-cyclopropano-6-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 13.6 percent / sulfuric acid/silica gel; water / dioxane / 0.17 h

2.1: 81.7 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 0 - 20 °C

3.1: ammonium formate / Pd/C / methanol; ethyl acetate / 2 h / Heating

4.1: 6.940 g / sodium hydrogencarbonate / acetone; H₂O / 0.33 h / 0 °C

5.1: p-toluenesulfonic anhydride; triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 5 h

5.2: 92.3 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 24 h

With dmap; sulfuric acid; p-toluenesulfonylanhydride; water; ammonium formate; silica gel; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; ethyl acetate; acetone;
DOI:10.1021/jo000250y