(-)-benzoic acid (1S,4S,4aS,5S,6R,8aS)-5-hydroxymethul-4,7-dimethyl-6-((E)-1-methyl-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester

Base Information

Chemical Name:(-)-benzoic acid (1S,4S,4aS,5S,6R,8aS)-5-hydroxymethul-4,7-dimethyl-6-((E)-1-methyl-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester
CAS No.:669010-41-7
Molecular Formula:C₂₄H₃₂O₃
Molecular Weight:368.516
Hs Code.:

Synonyms:(-)-benzoic acid (1S,4S,4aS,5S,6R,8aS)-5-hydroxymethul-4,7-dimethyl-6-((E)-1-methyl-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester

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Chemical Property of (-)-benzoic acid (1S,4S,4aS,5S,6R,8aS)-5-hydroxymethul-4,7-dimethyl-6-((E)-1-methyl-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester

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Technology Process of (-)-benzoic acid (1S,4S,4aS,5S,6R,8aS)-5-hydroxymethul-4,7-dimethyl-6-((E)-1-methyl-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester

There total 14 articles about (-)-benzoic acid (1S,4S,4aS,5S,6R,8aS)-5-hydroxymethul-4,7-dimethyl-6-((E)-1-methyl-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester 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: 89.0%

: 669010-52-0
Benzoic acid (1S,4S,4aS,5S,6R,8aS)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4,7-dimethyl-6-((E)-1-methyl-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester

: 669010-41-7
(-)-benzoic acid (1S,4S,4aS,5S,6R,8aS)-5-hydroxymethul-4,7-dimethyl-6-((E)-1-methyl-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol036338q

Reference yield:

: 669010-36-0
[(1S,2S,4aS,5S,8S,8aS)-2-(1-Ethoxy-ethoxymethyl)-3,8-dimethyl-5-triisopropylsilanyloxy-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-methanol

: 669010-41-7
(-)-benzoic acid (1S,4S,4aS,5S,6R,8aS)-5-hydroxymethul-4,7-dimethyl-6-((E)-1-methyl-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 98 percent / imidazole / CH₂Cl₂ / 20 °C

2.1: 87 percent / HCl / tetrahydrofuran / 20 °C

3.1: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

4.1: 93 percent / PPh₃ / CH₂Cl₂ / 20 °C

5.1: 73 percent / n-BuLi / tetrahydrofuran / -78 - 0 °C

6.1: Cp₂ZrCl₂ / H₂O; CH₂Cl₂ / -20 - 0 °C

6.2: 86 percent / I₂ / tetrahydrofuran / 0 °C

7.1: 99 percent / PdCl₂(PPh₃)2 / tetrahydrofuran / 20 °C

8.1: 95 percent / TBAG / tetrahydrofuran / Heating

9.1: 86 percent / imidazole / CH₂Cl₂ / 20 °C

10.1: 93 percent / DMAP / CH₂Cl₂ / 0 - 20 °C

11.1: 89 percent / TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; n-butyllithium; tetrabutyl ammonium fluoride; Dess-Martin periodane; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; zirconocene dichloride; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol036338q

Reference yield:

: 669010-34-8
(1S,2S,4aS,5S,8S,8aR)-2-Hydroxymethyl-3,8-dimethyl-5-triisopropylsilanyloxy-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methoxy-methyl-amide

: 669010-41-7
(-)-benzoic acid (1S,4S,4aS,5S,6R,8aS)-5-hydroxymethul-4,7-dimethyl-6-((E)-1-methyl-propenyl)-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-1-yl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 90 percent / PPTS / CH₂Cl₂ / 20 °C

2.1: 89 percent / BH₃-NH₃; LDA / tetrahydrofuran / 0 - 20 °C

3.1: 98 percent / imidazole / CH₂Cl₂ / 20 °C

4.1: 87 percent / HCl / tetrahydrofuran / 20 °C

5.1: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

6.1: 93 percent / PPh₃ / CH₂Cl₂ / 20 °C

7.1: 73 percent / n-BuLi / tetrahydrofuran / -78 - 0 °C

8.1: Cp₂ZrCl₂ / H₂O; CH₂Cl₂ / -20 - 0 °C

8.2: 86 percent / I₂ / tetrahydrofuran / 0 °C

9.1: 99 percent / PdCl₂(PPh₃)2 / tetrahydrofuran / 20 °C

10.1: 95 percent / TBAG / tetrahydrofuran / Heating

11.1: 86 percent / imidazole / CH₂Cl₂ / 20 °C

12.1: 93 percent / DMAP / CH₂Cl₂ / 0 - 20 °C

13.1: 89 percent / TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; n-butyllithium; borane-ammonia complex; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; triphenylphosphine; lithium diisopropyl amide; bis-triphenylphosphine-palladium(II) chloride; zirconocene dichloride; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol036338q