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

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)pentanoic acid
CAS No.:871095-02-2
Molecular Formula:C₃₀H₄₆O₃Si
Molecular Weight:482.779
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)pentanoic acid

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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)pentanoic acid

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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)pentanoic acid

There total 21 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)pentanoic 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: 99.0%

: 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

: 871095-02-2
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

Guidance literature:: With sodium chlorite; potassium dihydrogenphosphate; 2,3-Dimethyl-2-butene; In water; tert-butyl alcohol; at 0 - 20 ℃;
DOI:10.1021/ol0515762

Reference yield:

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

: 871095-02-2
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

Guidance literature:: Multi-step reaction with 7 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

7.1: 99 percent / 2,3-dimethyl-2-butene; sodium chlorite; potassium dihydrogen phosphate / 2-methyl-propan-2-ol; H₂O / 0 - 20 °C

With sodium chlorite; potassium dihydrogenphosphate; 2,3-Dimethyl-2-butene; 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; water; toluene; tert-butyl alcohol; 3.1: Swern oxidation / 4.2: Julia-Kocienski olefination / 6.1: Swern oxidation / 7.1: Pinnick oxidation;
DOI:10.1021/ol0515762

Reference yield:

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

: 871095-02-2
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

Guidance literature:: Multi-step reaction with 9 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

9.1: 99 percent / 2,3-dimethyl-2-butene; sodium chlorite; potassium dihydrogen phosphate / 2-methyl-propan-2-ol; H₂O / 0 - 20 °C

With dmap; sodium chlorite; potassium dihydrogenphosphate; 2,3-Dimethyl-2-butene; 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; water; toluene; tert-butyl alcohol; 5.1: Swern oxidation / 6.2: Julia-Kocienski olefination / 8.1: Swern oxidation / 9.1: Pinnick oxidation;
DOI:10.1021/ol0515762