(2aR,2a⁽¹⁾R,4R,5aS,5bS,8R,8aS)-methyl 5b-acetoxy-8-hydroxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyldecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate

Base Information

• Chemical Name: (2aR,2a⁽¹⁾R,4R,5aS,5bS,8R,8aS)-methyl 5b-acetoxy-8-hydroxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyldecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate
• CAS No.: 1384835-10-2
• Molecular Formula: C₂₇H₃₇NO₇
• Molecular Weight: 487.593

Synonyms:(2aR,2a⁽¹⁾R,4R,5aS,5bS,8R,8aS)-methyl 5b-acetoxy-8-hydroxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyldecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate

Chemical Property of (2aR,2a⁽¹⁾R,4R,5aS,5bS,8R,8aS)-methyl 5b-acetoxy-8-hydroxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyldecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of (2aR,2a⁽¹⁾R,4R,5aS,5bS,8R,8aS)-methyl 5b-acetoxy-8-hydroxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyldecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate

There total 10 articles about (2aR,2a⁽¹⁾R,4R,5aS,5bS,8R,8aS)-methyl 5b-acetoxy-8-hydroxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a⁽¹⁾-methyldecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-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: 95.0%

(2aR,2a(1)R,4R,5aS,5bS,8aR)methyl 5b-acetoxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a(1)-methyl-8-oxodecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate (1384835-08-8) → (2aR,2a(1)R,4R,5aS,5bS,8R,8aS)-methyl 5b-acetoxy-8-hydroxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a(1)-methyldecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate (1384835-10-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo300776d

Reference yield:

C17H24O4S (1384834-98-3) → (2aR,2a(1)R,4R,5aS,5bS,8R,8aS)-methyl 5b-acetoxy-8-hydroxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a(1)-methyldecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate (1384835-10-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.67 h / 0 °C / Inert atmosphere

2.2: 6 h / Reflux; Inert atmosphere

3.1: toluene-4-sulfonic acid / methanol; N,N-dimethyl-formamide / 1 h / Reflux; Inert atmosphere

3.2: 4 h / 150 °C / Inert atmosphere

4.1: potassium tert-butylate / tert-butyl alcohol / 1.5 h / 20 °C / Inert atmosphere

5.1: Sn(NTf₂)4*9DMSO / acetonitrile / 4 h / 20 °C / Inert atmosphere

6.1: triethylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

7.1: acetonitrile / 0.25 h / 0 °C / Inert atmosphere; UV-irradiation

8.1: sodium tetrahydroborate / methanol / 2 h / 0 °C / Inert atmosphere

With sodium tetrahydroborate; Sn(NTf₂)4*9DMSO; potassium tert-butylate; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 2.1: Overman rearrangement / 2.2: Overman rearrangement;

DOI:10.1021/jo300776d

Reference yield:

methyl (hydroxymethyl) ((1R,5R)-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)carbamate (1384835-05-5) → (2aR,2a(1)R,4R,5aS,5bS,8R,8aS)-methyl 5b-acetoxy-8-hydroxy-4-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2a(1)-methyldecahydrocyclopenta[1,4]cyclobuta[1,2,3-cd]indole-1-carboxylate (1384835-10-2)

Guidance literature:

Multi-step reaction with 4 steps

1: Sn(NTf₂)4*9DMSO / acetonitrile / 4 h / 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere

3: acetonitrile / 0.25 h / 0 °C / Inert atmosphere; UV-irradiation

4: sodium tetrahydroborate / methanol / 2 h / 0 °C / Inert atmosphere

With sodium tetrahydroborate; Sn(NTf₂)4*9DMSO; triethylamine; In methanol; dichloromethane; acetonitrile;

DOI:10.1021/jo300776d

upstream raw materials:

C₁₇H₂₄O₄S

(1S,5S)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enol

2,2,2-trichloro-N-((1R,5R)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enyl)acetamide

methyl (1R,5R)-5-((S)-1-(4-methoxyphenoxy)propan-2-yl)-2-methylcyclohex-2-enylcarbamate

Downstream raw materials:

C₂₈H₃₉NO₉S

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