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

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)pentanal
CAS No.:871095-07-7
Molecular Formula:C₃₀H₄₆O₂Si
Molecular Weight:466.78
Hs Code.:

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)pentanal

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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)pentanal

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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)pentanal

There total 20 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)pentanal 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: 100.0%

: 871095-01-1
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

: 871095-07-7
5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentanal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃; for 2.5h;
DOI:10.1021/ol0515762

Reference yield:

: 286440-95-7
1-[(5-bromopentyloxy)methyl]-4-methoxybenzene

: 871095-07-7
5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentanal

Guidance literature:: Multi-step reaction with 6 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

6.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 2.5 h / -78 - 0 °C

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 / 6.1: Swern oxidation;
DOI:10.1021/ol0515762

Reference yield:

: 871095-04-4
(3aS,4S,5R,6aR)-5-((tert-butyldimethylsilyl)oxy)-4-(hydroxymethyl)hexahydropentalen-2(1H)-one

: 871095-07-7
5-((3aS,5R,6R,6aS)-5-(tert-butyldimethylsilyloxy)-6-((E)-4-m-tolylbut-1-enyl)-1,3a,4,5,6,6a-hexahydropentalen-2-yl)pentanal

Guidance literature:: Multi-step reaction with 8 steps

1.1: 97 percent / triethylamine; DMAP / CH₂Cl₂ / 5 h / 20 °C

2.1: KHMDS / tetrahydrofuran; toluene / 5 h / -108 °C

2.2: tetrahydrofuran; toluene / -108 - 20 °C

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

3.2: LiCl / Pd(PPh₃)4 / diethyl ether

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

5.1: 2.2 g / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 2.5 h / -78 - 0 °C

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

6.2: 95.4 percent / 1,2-dimethoxy-ethane; toluene / -60 - 20 °C

7.1: 85 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h

8.1: 100 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 2.5 h / -78 - 0 °C

With dmap; oxalyl dichloride; 1,1-Dibromoethane; water; diethylaluminium chloride; potassium hexamethylsilazane; magnesium; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; toluene; 5.1: Swern oxidation / 6.2: Julia-Kocienski olefination / 8.1: Swern oxidation;
DOI:10.1021/ol0515762