4-benzyloxy-3-{(2'E)-3'-methyl-5'-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthyl]-2'-pentenyl}benzoic acid

Base Information

Chemical Name:4-benzyloxy-3-{(2'E)-3'-methyl-5'-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthyl]-2'-pentenyl}benzoic acid
CAS No.:534600-70-9
Molecular Formula:C₃₄H₄₄O₃
Molecular Weight:500.722
Hs Code.:

Synonyms:4-benzyloxy-3-{(2'E)-3'-methyl-5'-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthyl]-2'-pentenyl}benzoic acid

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Chemical Property of 4-benzyloxy-3-{(2'E)-3'-methyl-5'-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthyl]-2'-pentenyl}benzoic acid

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Technology Process of 4-benzyloxy-3-{(2'E)-3'-methyl-5'-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthyl]-2'-pentenyl}benzoic acid

There total 19 articles about 4-benzyloxy-3-{(2'E)-3'-methyl-5'-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthyl]-2'-pentenyl}benzoic 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:

: 534600-69-6
3-[(E)-5-Benzenesulfonyl-3-methyl-5-((4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pent-2-enyl]-4-benzyloxy-benzoic acid benzyl ester

: 534600-70-9
4-benzyloxy-3-{(2'E)-3'-methyl-5'-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthyl]-2'-pentenyl}benzoic acid

Guidance literature:: With disodium hydrogenphosphate; sodium amalgam; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 17h;
DOI:10.1002/ejoc.200390128

Reference yield:

: 1138-41-6
4-hydroxy-3-prenylbenzoic acid

: 534600-70-9
4-benzyloxy-3-{(2'E)-3'-methyl-5'-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthyl]-2'-pentenyl}benzoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: 7.5 g / K₂CO₃ / dimethylformamide / 15 h / 20 °C

2.1: SeO₂; tBuO₂H / CH₂Cl₂ / 71 h / 20 °C

2.2: 45 percent / NaBH₄ / tetrahydrofuran; H₂O / 2.5 h / 0 - 20 °C

3.1: 87 percent / Ms₂O; LiBr; collidine / DMAP / dimethylformamide / 24 h / 0 °C

4.1: 1.71 g / nBuLi; HMPA / hexane; tetrahydrofuran / 2.5 h / -65 °C

5.1: 468 mg / Na/Hg; Na₂HPO₄ / tetrahydrofuran; methanol / 17 h / 0 - 20 °C

With 2,3,5-trimethyl-pyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; selenium(IV) oxide; potassium carbonate; lithium bromide; Methanesulfonic anhydride; dmap; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200390128

Reference yield:

: 172788-55-5
Methyl <(S)-5-(benzyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl>-3-oxopentanoate

: 534600-70-9
4-benzyloxy-3-{(2'E)-3'-methyl-5'-[(4aR,8aR)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthyl]-2'-pentenyl}benzoic acid

Guidance literature:: Multi-step reaction with 13 steps

1.1: SnCl₄ / CH₂Cl₂

2.1: 76 percent / TMSOTf / CH₂Cl₂ / 20 h / -78 - 0 °C

3.1: 80 percent / H₂ / Pd/C / ethyl acetate / 11 h / 20 °C

4.1: 90 percent / trifluoromethanesulfonyl chloride; DMAP / CH₂Cl₂ / 2 h / 20 °C

5.1: 100 percent / H₂ / Pd/C / ethyl acetate / 19 h / 20 °C

6.1: 91 percent / aq. HCl / tetrahydrofuran / 24 h / 20 °C

7.1: NaH / tetrahydrofuran / 1 h / Heating

7.2: 89 percent / NaH / tetrahydrofuran / 2 h / 20 °C

8.1: CuI / diethyl ether / 1 h / -20 °C

8.2: 87 percent / diethyl ether / 6 h / -10 °C

9.1: 95 percent / DIBAL / hexane; CH₂Cl₂ / 2 h / -65 °C

10.1: MsCl; collidine; LiCl / dimethylformamide / 46 h / 5 °C

11.1: 2.3 g / dimethylformamide / 48 h / 20 °C

12.1: 1.71 g / nBuLi; HMPA / hexane; tetrahydrofuran / 2.5 h / -65 °C

13.1: 468 mg / Na/Hg; Na₂HPO₄ / tetrahydrofuran; methanol / 17 h / 0 - 20 °C

With 2,3,5-trimethyl-pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; disodium hydrogenphosphate; sodium amalgam; copper(l) iodide; n-butyllithium; trifluoromethane sulfonyl chloride; trimethylsilyl trifluoromethanesulfonate; hydrogen; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200390128