methyl (3aRS,4RS,11bSR,6SR)-3-benzyl-4-[2-(tert-butyldimethylsilyloxymethyl)phenyl]-2,3,3a,4,5,6-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-(15-vindolinyl)-6-carboxylate

Base Information

• Chemical Name: methyl (3aRS,4RS,11bSR,6SR)-3-benzyl-4-[2-(tert-butyldimethylsilyloxymethyl)phenyl]-2,3,3a,4,5,6-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-(15-vindolinyl)-6-carboxylate
• CAS No.: 634597-55-0
• Molecular Formula: C₆₁H₇₄N₄O₉Si
• Molecular Weight: 1035.37

Synonyms:

Chemical Property of methyl (3aRS,4RS,11bSR,6SR)-3-benzyl-4-[2-(tert-butyldimethylsilyloxymethyl)phenyl]-2,3,3a,4,5,6-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-(15-vindolinyl)-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of methyl (3aRS,4RS,11bSR,6SR)-3-benzyl-4-[2-(tert-butyldimethylsilyloxymethyl)phenyl]-2,3,3a,4,5,6-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-(15-vindolinyl)-6-carboxylate

There total 5 articles about methyl (3aRS,4RS,11bSR,6SR)-3-benzyl-4-[2-(tert-butyldimethylsilyloxymethyl)phenyl]-2,3,3a,4,5,6-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-(15-vindolinyl)-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:

3-benzyl-4-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-6-chloro-2,3,3a,4,5,6-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylic acid methyl ester + vindoline hydrochloride (5826-69-7) → methyl (3aRS,4RS,11bSR,6SR)-3-benzyl-4-[2-(tert-butyldimethylsilyloxymethyl)phenyl]-2,3,3a,4,5,6-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-(15-vindolinyl)-6-carboxylate (634597-55-0)

Guidance literature:

With silver tetrafluoroborate; In acetone; at 0 ℃; for 0.5h;

DOI:10.1039/b209990j

Reference yield:

isochroman-3-one (4385-35-7) → methyl (3aRS,4RS,11bSR,6SR)-3-benzyl-4-[2-(tert-butyldimethylsilyloxymethyl)phenyl]-2,3,3a,4,5,6-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-(15-vindolinyl)-6-carboxylate (634597-55-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 91 percent / DIBAL-H / CH₂Cl₂ / 3 h / -78 °C

2.1: B(OH)3 / CH₂Cl₂ / 72 h / 20 °C

2.2: CHCl₃ / 8 h / Heating

2.3: 50 percent / Et₃N / methanol / 10 h / Heating

3.1: 93 percent / Et₃N / CH₂Cl₂ / 0.08 h / 20 °C

4.1: tert-butyl hypochlorite; Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

5.1: AgBF₄ / acetone / 0.5 h / 0 °C

With silver tetrafluoroborate; tert-butylhypochlorite; boric acid; diisobutylaluminium hydride; triethylamine; In dichloromethane; acetone;

DOI:10.1039/b209990j

Reference yield:

3,4-dihydro-1H-2-benzopyran-3-ol (42900-89-0) → methyl (3aRS,4RS,11bSR,6SR)-3-benzyl-4-[2-(tert-butyldimethylsilyloxymethyl)phenyl]-2,3,3a,4,5,6-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-(15-vindolinyl)-6-carboxylate (634597-55-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: B(OH)3 / CH₂Cl₂ / 72 h / 20 °C

1.2: CHCl₃ / 8 h / Heating

1.3: 50 percent / Et₃N / methanol / 10 h / Heating

2.1: 93 percent / Et₃N / CH₂Cl₂ / 0.08 h / 20 °C

3.1: tert-butyl hypochlorite; Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

4.1: AgBF₄ / acetone / 0.5 h / 0 °C

With silver tetrafluoroborate; tert-butylhypochlorite; boric acid; triethylamine; In dichloromethane; acetone;

DOI:10.1039/b209990j

upstream raw materials:

vindoline hydrochloride

isochroman-3-one

3,4-dihydro-1H-2-benzopyran-3-ol

Downstream raw materials:

methyl (5S,7R)-3-benzyl-5-[2-(tert-butyldimethylsilyloxymethyl)phenyl]-1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]indole-7-(15-vindolinyl)-7-carboxylate

methyl (5R,7S)-3-benzyl-5-[2-(tert-butyldimethylsilyloxymethyl)phenyl]-1,2,3,4,5,6,7,8-octahydroazonino[5,4-b]indole-7-(15-vindolinyl)-7-carboxylate

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