6-[(S)-2-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-hydroxy-cyclohex-(E)-ylidene]-hexanoic acid

Base Information

• Chemical Name: 6-[(S)-2-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-hydroxy-cyclohex-(E)-ylidene]-hexanoic acid
• CAS No.: 84458-86-6
• Molecular Formula: C₃₂H₅₂O₃
• Molecular Weight: 484.763
• Mol file: 84458-86-6.mol

Synonyms:6-[(S)-2-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-hydroxy-cyclohex-(E)-ylidene]-hexanoic acid

Chemical Property of 6-[(S)-2-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-hydroxy-cyclohex-(E)-ylidene]-hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[(S)-2-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-hydroxy-cyclohex-(E)-ylidene]-hexanoic acid

There total 6 articles about 6-[(S)-2-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-hydroxy-cyclohex-(E)-ylidene]-hexanoic acid 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: 73.0%

5-{(S)-3-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-5-hydroxy-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-1-yl}-pentanoic acid (86847-15-6) → 6-[(S)-2-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-hydroxy-cyclohex-(E)-ylidene]-hexanoic acid (84458-86-6) + (5E)-Vitamin D3 19-Pentanoic Acid (86900-18-7)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; at 95 ℃; for 3.5h; sealed tube;

DOI:10.1021/jo00168a021

Reference yield:

5-iodovaleric acid tert-butyl ester (56198-37-9) → 6-[(S)-2-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-hydroxy-cyclohex-(E)-ylidene]-hexanoic acid (84458-86-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 49 percent / lithium tetramethylpiperidine (LiTMP) / tetrahydrofuran; 1,2-dimethoxy-ethane; pentane / 1 h / -75 °C

2: 83 percent / trifluoroacetic acid / CH₂Cl₂ / 1) 0 degC, 30 min, 2) room temp., 1.5 h

3: NaHCO₃ / aq. ethanol / 3.5 h / 95 °C / sealed tube

With 2,2,6,6-tetramethylpiperidinyl-lithium; sodium hydrogencarbonate; trifluoroacetic acid; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; pentane;

DOI:10.1021/jo00168a021

Reference yield:

5-[(S)-3-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-5-(tetrahydro-pyran-2-yloxy)-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-1-yl]-pentanoic acid tert-butyl ester (86847-14-5) → 6-[(S)-2-[2-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-hydroxy-cyclohex-(E)-ylidene]-hexanoic acid (84458-86-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / trifluoroacetic acid / CH₂Cl₂ / 1) 0 degC, 30 min, 2) room temp., 1.5 h

2: NaHCO₃ / aq. ethanol / 3.5 h / 95 °C / sealed tube

With sodium hydrogencarbonate; trifluoroacetic acid; In ethanol; dichloromethane;

DOI:10.1021/jo00168a021

upstream raw materials:

5-{(S)-3-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-5-hydroxy-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-1-yl}-pentanoic acid

5-iodovaleric acid tert-butyl ester

5-[(S)-3-[(1R,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-5-(tetrahydro-pyran-2-yloxy)-2,3,4,5,6,7-hexahydro-1H-2λ⁶-benzo[c]thiophen-1-yl]-pentanoic acid tert-butyl ester

vitamin D₃