ethyl (4aR,6S,8aS)-3-[(6-benzyloxy-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthyl)methyl]-2,4-dihydroxy-6-methylbenzoate

Base Information

Chemical Name:ethyl (4aR,6S,8aS)-3-[(6-benzyloxy-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthyl)methyl]-2,4-dihydroxy-6-methylbenzoate
CAS No.:299428-91-4
Molecular Formula:C₃₂H₄₂O₅
Molecular Weight:506.682
Hs Code.:

Synonyms:ethyl (4aR,6S,8aS)-3-[(6-benzyloxy-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthyl)methyl]-2,4-dihydroxy-6-methylbenzoate

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Chemical Property of ethyl (4aR,6S,8aS)-3-[(6-benzyloxy-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthyl)methyl]-2,4-dihydroxy-6-methylbenzoate

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Technology Process of ethyl (4aR,6S,8aS)-3-[(6-benzyloxy-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthyl)methyl]-2,4-dihydroxy-6-methylbenzoate

There total 3 articles about ethyl (4aR,6S,8aS)-3-[(6-benzyloxy-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthyl)methyl]-2,4-dihydroxy-6-methylbenzoate 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:

: 299428-90-3
3-((4aR,6S,8aS)-6-Benzyloxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl)-6-methyl-2,4-bis-(2-trimethylsilanyl-ethoxymethoxy)-benzoic acid ethyl ester

: 299428-91-4
ethyl (4aR,6S,8aS)-3-[(6-benzyloxy-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthyl)methyl]-2,4-dihydroxy-6-methylbenzoate

Guidance literature:: With sulfuric acid; In tetrahydrofuran; ethanol; at 20 ℃; for 15h;
DOI:10.1271/bbb.64.1410

Reference yield:

: 115404-48-3
(3S,4aR,8aS)-3-Benzyloxy-8-bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

: 299428-91-4
ethyl (4aR,6S,8aS)-3-[(6-benzyloxy-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthyl)methyl]-2,4-dihydroxy-6-methylbenzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: CuCN / hexane; tetrahydrofuran / -78 - -10 °C

1.3: tetrahydrofuran; hexane / 2 h / -78 °C

2.1: 455 mg / H₂SO₄ / ethanol; tetrahydrofuran / 15 h / 20 °C

With n-butyllithium; sulfuric acid; In tetrahydrofuran; ethanol; hexane; 1.1: Metallation / 1.2: Metallation / 1.3: Substitution / 2.1: Substitution;
DOI:10.1271/bbb.64.1410

Reference yield:

: 115333-56-7
(4aR,6S,8aS)-(+)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-1-hydroxymethyl-2,5,5,8a-tetramethylnaphthalene

: 299428-91-4
ethyl (4aR,6S,8aS)-3-[(6-benzyloxy-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthyl)methyl]-2,4-dihydroxy-6-methylbenzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: PBr₃ / diethyl ether / -20 °C

2.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: CuCN / hexane; tetrahydrofuran / -78 - -10 °C

2.3: tetrahydrofuran; hexane / 2 h / -78 °C

3.1: 455 mg / H₂SO₄ / ethanol; tetrahydrofuran / 15 h / 20 °C

With n-butyllithium; sulfuric acid; phosphorus tribromide; In tetrahydrofuran; diethyl ether; ethanol; hexane; 1.1: Substitution / 2.1: Metallation / 2.2: Metallation / 2.3: Substitution / 3.1: Substitution;
DOI:10.1271/bbb.64.1410