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

Base Information

Chemical Name:[2R,4aS,6R,8aS]-4-(6-benzyloxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-ylmethyl)-3,5-dihydroxybenzoic acid methyl ester
CAS No.:541501-09-1
Molecular Formula:C₃₀H₃₈O₅
Molecular Weight:478.629
Hs Code.:

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

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Chemical Property of [2R,4aS,6R,8aS]-4-(6-benzyloxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-ylmethyl)-3,5-dihydroxybenzoic acid methyl ester

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Technology Process of [2R,4aS,6R,8aS]-4-(6-benzyloxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-ylmethyl)-3,5-dihydroxybenzoic acid methyl ester

There total 10 articles about [2R,4aS,6R,8aS]-4-(6-benzyloxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-ylmethyl)-3,5-dihydroxybenzoic 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: 94.0%

: 541501-08-0
3,5-Bis-benzyloxy-4-((4aR,6R,8aS)-6-benzyloxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-benzoic acid methyl ester

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

Guidance literature:: With hydrogen; nickel; In tetrahydrofuran; water;
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

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

Guidance literature:: Multi-step reaction with 7 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

With n-butyllithium; thionyl chloride; 4 A molecular sieve; hydrogen; trimethyl(benzyl)ammonium fluoride; nickel; sodium cyanoborohydride; zinc(II) iodide; lithium diisopropyl amide; In tetrahydrofuran; 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

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

Guidance literature:: Multi-step reaction with 2 steps

1: thionyl chloride / 2.5 h / Heating

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

With thionyl chloride; hydrogen; nickel; In tetrahydrofuran; water;