5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentan-1-ol

Base Information

• Chemical Name: 5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentan-1-ol
• CAS No.: 871095-01-1
• Molecular Formula: C₃₀H₄₈O₂Si
• Molecular Weight: 468.795
• Mol file: 871095-01-1.mol

Synonyms:5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentan-1-ol

Chemical Property of 5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentan-1-ol

There total 29 articles about 5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentan-1-ol 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: 85.0%

tert-butyl((1R,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-((E)-4-m-tolylbut-1-enyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane (871095-00-0) → 5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentan-1-ol (871095-01-1)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 0.5h;

DOI:10.1021/ol0515762

Reference yield: 64.0%

tert-butyldimethyl{(2R,3R,3aS,6aS)-5-[5-(tetrahydro-2H-pyran-2-yloxy)pentyl]-3-[(E)-4-m-tolylbut-1-enyl]-1,2,3,3a,4,6a-hexahydropentalen-2-yloxy}silane (934968-46-4) → 5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentan-1-ol (871095-01-1)

Guidance literature:

With magnesium bromide; In diethyl ether;

DOI:10.1002/chem.200600728

Reference yield:

1-[(5-bromopentyloxy)methyl]-4-methoxybenzene (286440-95-7) → 5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentan-1-ol (871095-01-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Mg; dibromoethane / diethyl ether / 4 h / 10 °C

1.2: LiCl / Pd(PPh₃)4 / diethyl ether

2.1: Et₂AlCl / CH₂Cl₂; toluene / 3 h / -50 °C

3.1: 2.2 g / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 2.5 h / -78 - 0 °C

4.1: KHMDS / 1,2-dimethoxy-ethane; toluene / 0.75 h / -60 °C

4.2: 95.4 percent / 1,2-dimethoxy-ethane; toluene / -60 - 20 °C

5.1: 85 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h

With oxalyl dichloride; 1,1-Dibromoethane; water; diethylaluminium chloride; potassium hexamethylsilazane; magnesium; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dimethoxyethane; diethyl ether; dichloromethane; toluene; 3.1: Swern oxidation / 4.2: Julia-Kocienski olefination;

DOI:10.1021/ol0515762

upstream raw materials:

tert-butyl((1R,2R,3aS,6aS)-5-(5-(4-methoxybenzyloxy)pentyl)-1-((E)-4-m-tolylbut-1-enyl)-1,2,3,3a,6,6a-hexahydropentalen-2-yloxy)dimethylsilane

tert-butyldimethyl{(2R,3R,3aS,6aS)-5-[5-(tetrahydro-2H-pyran-2-yloxy)pentyl]-3-[(E)-4-m-tolylbut-1-enyl]-1,2,3,3a,4,6a-hexahydropentalen-2-yloxy}silane

(3a'S,4'R,5'R,6a'R)-5,5-dimethyl-4'-[(E)-4-m-tolylbut-1-enyl]hexahydro-1'H-spiro([1,3]dioxane-2,2'-pentalen)-5'-ol

(3aS,4R,5R,6aR)-5-hydroxy-4-[(E)-4-m-tolylbut-1-enyl]hexahydropentalen-2(1H)-one

Downstream raw materials:

5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentanoic acid

5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentanal