(3aS,4S)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2,3-dihydroxypropyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

Base Information

• Chemical Name: (3aS,4S)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2,3-dihydroxypropyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate
• CAS No.: 131829-82-8
• Molecular Formula: C₂₈H₃₄N₂O₄
• Molecular Weight: 462.589
• Mol file: 131829-82-8.mol

Synonyms:

Chemical Property of (3aS,4S)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2,3-dihydroxypropyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2,3-dihydroxypropyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

There total 1 articles about (3aS,4S)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2,3-dihydroxypropyl>-1H-pyrrolo<2,3-d>carbazole-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:

(4R)-4-ethyl-4,5-dihydroxypentanal acetonide (131703-67-8) + methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (66859-30-1) → (3aR,4R)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2,3-dihydroxypropyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (131829-79-3) + (3aS,4S)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2,3-dihydroxypropyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (131829-82-8)

Guidance literature:

With hydrogenchloride; Yield given. Multistep reaction. Yields of byproduct given; 1.) toluene, reflux, 12 h, 2.) methanol, reflux, 20 min;

DOI:10.1021/jo00002a008

Reference yield:

(3aS,4S)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2,3-dihydroxypropyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (131829-82-8) → (3aS,4S)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2-<(trimethylsilyl)oxy>-3-<(p-tolylsulfonyl)oxy>propyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (131829-75-9)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / CH₂Cl₂ / 24 h

2: triethylamine / tetrahydrofuran / 0.5 h / 0 °C

With triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00002a008

Reference yield:

(3aS,4S)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2,3-dihydroxypropyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (131829-82-8) → (3aS,4R,11bR)-3-Benzyl-6-chloro-4-[(R)-2-(toluene-4-sulfonyloxymethyl)-2-trimethylsilanyloxy-butyl]-2,3,3a,4,5,6-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester (131703-71-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / CH₂Cl₂ / 24 h

2: triethylamine / tetrahydrofuran / 0.5 h / 0 °C

3: tert-butyl hypochlorite, triethylamine / CH₂Cl₂ / 0.08 h / 0 °C

With tert-butylhypochlorite; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00002a008

upstream raw materials:

(4R)-4-ethyl-4,5-dihydroxypentanal acetonide

methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate

Downstream raw materials:

(3aS,4S,11bR)-3-Benzyl-4-[(R)-2-hydroxy-2-(toluene-4-sulfonyloxymethyl)-butyl]-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester

(3aS,4S)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2R)-2-ethyl-2-<(trimethylsilyl)oxy>-3-<(p-tolylsulfonyl)oxy>propyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate

(3aS,4R,11bR)-3-Benzyl-6-chloro-4-[(R)-2-(toluene-4-sulfonyloxymethyl)-2-trimethylsilanyloxy-butyl]-2,3,3a,4,5,6-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester

(7R,5S)-methyl 3-benzyl-1,2,3,4,5,6,7,8-octahydro-5-((2R)-2-ethyl-2,3-epoxypropyl)-7-(15-vindolinyl)azonino[5,4-b]indole-7-carboxylate