(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

Base Information

• Chemical Name: (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
• CAS No.: 362517-09-7
• Molecular Formula: C₃₃H₄₀N₂O₆
• Molecular Weight: 560.69

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 4 articles about (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 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: 96.1%

2,2-dimethoxy-propane (77-76-9) + (3aR,4S,5S,11bS)-dimethyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-dihydroxypropyl]-1H-pyrrolo[2,3-d]carbazole-5,6-dicarboxylate (362517-07-5) → (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 (362517-09-7)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 2h; Heating;

DOI:10.1021/jo000250y

Reference yield: 13.6%

acetone (67-64-1) + (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 (362517-06-4) → (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 (362517-09-7) + (3aR,4S,5S,11bS)-dimethyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-[(2R)-2-ethyl-2,3-(dihydroxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-dicarboxylate (362517-04-2) + (3aR,4S,5S,11bS)-dimethyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-[(2S)-2-ethyl-2,3-dihydroxypropyl]-1H-pyrrolo[2,3-d]carbazole-5,6-dicarboxylate (362517-07-5)

Guidance literature:

With sulfuric acid; water; silica gel; In 1,4-dioxane; for 0.166667h;

DOI:10.1021/jo000250y

Reference yield:

(3aR,4S,5S,11bS)-dimethyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-[(2R)-2-ethyl-2,3-(dihydroxy)propyl]-1H-pyrrolo[2,3-d]carbazole-5,6-dicarboxylate (362517-04-2) → (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 (362517-09-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 98.7 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 5 h

2: 96.3 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 8 h

3: 13.6 percent / sulfuric acid/silica gel; water / dioxane / 0.17 h

With dmap; sulfuric acid; water; silica gel; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1021/jo000250y

upstream raw materials:

2,2-dimethoxy-propane

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

acetone

(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

Downstream raw materials:

(1S,5R,6R)-4-phenylmethyl-4,11-diaza-6-((1(S)-ethyl-3,3-dimethyl(2,4-dioxolanyl))methyl)-9-(methoxycarbonyl)tetracyclo[8.7.0.0^1,5.0^12,17]heptadeca-9,12⁽¹³⁾,14,16-tetraene-4-carboxylate

(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

C₃₃H₄₀N₂O₆

(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

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