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

Base Information

• Chemical Name: (3aR,4R)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2S)-2-ethyl-2-<(trimethylsilyl)oxy>-3-<(p-tolylsulfonyl)oxy>propyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate
• CAS No.: 131829-72-6
• Molecular Formula: C₃₈H₄₈N₂O₆SSi
• Molecular Weight: 688.96

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

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

There total 9 articles about (3aR,4R)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2S)-2-ethyl-2-<(trimethylsilyl)oxy>-3-<(p-tolylsulfonyl)oxy>propyl>-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: 92.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (3aR,4R)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2S)-2-ethyl-2-hydroxy-3-<(p-tolylsulfonyl)oxy>propyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (131829-78-2) → (3aR,4R)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2S)-2-ethyl-2-<(trimethylsilyl)oxy>-3-<(p-tolylsulfonyl)oxy>propyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (131829-72-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1021/jo00002a008

Reference yield:

2-Methylene-1-butanol (4435-54-5) → (3aR,4R)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2S)-2-ethyl-2-<(trimethylsilyl)oxy>-3-<(p-tolylsulfonyl)oxy>propyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (131829-72-6)

Guidance literature:

Multi-step reaction with 8 steps

1: L-(+)-diethyl tartrate, titanium(IV) isopropoxide, tert-butyl hydroperoxide, activated 4.0-Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 1.) -20 deg C, 4 h, 2.) -15 deg C, 12 h

2: 91 percent / copper iodide / tetrahydrofuran / 1.) -25 to -30 deg C, 6 h, 2.) -15 deg C, 12 h

3: 99 percent / p-toluenesulfonic acid / acetone / 12 h

4: 1.) ozone, 2.) triphenylphosphine / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) room temperature, 24 h

6: 110 mg / 10percent aq. HCl / methanol / 0.25 h / Heating

7: 76 percent / triethylamine / CH₂Cl₂ / 26 h

8: 92 percent / N,N-diisopropylethylamine / tetrahydrofuran / 0.25 h / 0 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; copper(l) iodide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; toluene-4-sulfonic acid; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; dichloromethane; acetone;

DOI:10.1021/jo00002a008

Reference yield:

p-toluenesulfonylanhydride (4124-41-8) → (3aR,4R)-methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-<(2S)-2-ethyl-2-<(trimethylsilyl)oxy>-3-<(p-tolylsulfonyl)oxy>propyl>-1H-pyrrolo<2,3-d>carbazole-6-carboxylate (131829-72-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / triethylamine / CH₂Cl₂ / 26 h

2: 92 percent / N,N-diisopropylethylamine / tetrahydrofuran / 0.25 h / 0 °C

With triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00002a008

upstream raw materials:

trimethylsilyl trifluoromethanesulfonate

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

2-Methylene-1-butanol

p-toluenesulfonylanhydride

Downstream raw materials:

C₆₃H₇₈N₄O₁₂SSi

(7S,5R)-methyl 3-benzyl-1,2,3,4,5,6,7,8-octahydro-5-<(2S)-2-ethyl-2-<(trimethylsilyl)oxy>-3-<(p-tolylsulfonyl)oxy>propyl>-7-(15-vindolinyl)azonino<5,4-b>indole-7-carboxylate

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

(3aR,4S,11bS)-3-Benzyl-6-chloro-4-[(S)-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

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