3,5-Dihydroxy-4-((4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester

Base Information

Chemical Name:3,5-Dihydroxy-4-((4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester
CAS No.:541501-10-4
Molecular Formula:C₂₃H₃₂O₅
Molecular Weight:388.504
Hs Code.:

Synonyms:3,5-Dihydroxy-4-((4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester

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Chemical Property of 3,5-Dihydroxy-4-((4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester

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Technology Process of 3,5-Dihydroxy-4-((4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester

There total 11 articles about 3,5-Dihydroxy-4-((4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl 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: 100.0%

: 541501-09-1
[2R,4aS,6R,8aS]-4-(6-benzyloxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-ylmethyl)-3,5-dihydroxybenzoic acid methyl ester

: 541501-10-4
3,5-Dihydroxy-4-((4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethanol;
DOI:10.1021/ol030039j

Reference yield:

: 155486-89-8
(-)-(4aS,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-5,5,8a-trimethyl-1(2H)-naphthalenone

: 541501-10-4
3,5-Dihydroxy-4-((4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h / -20 - 0 °C

1.2: tetrahydrofuran; hexane / 0.5 h / 0 °C

2.1: molecular sieves 4 Angstroem; benzyltrimethylammonium fluoride / tetrahydrofuran / 4 h / 20 °C

2.2: 2.16 g / hydrazine; AcOH / ethanol / Heating

3.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: tetrahydrofuran; hexane / 2 h / -78 - 0 °C

4.1: 1.81 g / NaBH₃CN; ZnI₂ / CH₂Cl₂ / 4 h / 0 °C

5.1: thionyl chloride / 2.5 h / Heating

6.1: 66 mg / Raney Ni; hydrogen / tetrahydrofuran; H₂O / 16 h

7.1: hydrogen / Pd/C / ethanol / 8 h

With n-butyllithium; thionyl chloride; 4 A molecular sieve; hydrogen; trimethyl(benzyl)ammonium fluoride; nickel; sodium cyanoborohydride; zinc(II) iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; water;

Reference yield:

: 541501-07-9
[2R,4aS,6R,8aS]-3,5-bis(benzyloxy)-4-(6-benzyloxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-ylmethyl)benzoic acid tert-butyl ester

: 541501-10-4
3,5-Dihydroxy-4-((4aR,6R,8aS)-6-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: thionyl chloride / 2.5 h / Heating

2: 66 mg / Raney Ni; hydrogen / tetrahydrofuran; H₂O / 16 h

3: hydrogen / Pd/C / ethanol / 8 h

With thionyl chloride; hydrogen; nickel; palladium on activated charcoal; In tetrahydrofuran; ethanol; water;