(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid 1,1-dimethylethyl ester

Base Information

Chemical Name:(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid 1,1-dimethylethyl ester
CAS No.:652153-18-9
Molecular Formula:C₂₅H₃₄O₄
Molecular Weight:398.543
Hs Code.:

Synonyms:(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid 1,1-dimethylethyl ester

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Chemical Property of (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid 1,1-dimethylethyl ester

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Technology Process of (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid 1,1-dimethylethyl ester

There total 6 articles about (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid 1,1-dimethylethyl 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: 92.0%

: 652153-24-7
3-((4aR,6R,8aR)-6-Benzyloxy-8a-methyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-hydroxy-propionic acid tert-butyl ester

: 652153-18-9
(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid 1,1-dimethylethyl ester

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.75h;
DOI:10.1002/hlca.200390315

Reference yield:

: (4aR,6R,8aR)-6-Benzyloxy-8a-methyl-octahydro-naphthalen-1-one

: 652153-18-9
(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid 1,1-dimethylethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 90 percent / Proton Sponge(R) / CH₂Cl₂ / 16 h / 20 °C

2.1: 83 percent / K₂CO₃; LiCl; 1-methylpyrrolidin-2-one / dichlorobis(triphenylphosphine)palladium / 24 h / 130 °C / 10343 Torr

3.1: 86 percent / Dibal-H / CH₂Cl₂ / -78 °C

4.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

5.1: Zn; I₂ / diethyl ether / 2 h / 20 °C

5.2: 87 percent / diethyl ether / 3 h / 20 °C

6.1: 92 percent / Dess-Martin periodianne / CH₂Cl₂ / 0.75 h / 20 °C

With 1-methyl-pyrrolidin-2-one; iodine; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; lithium chloride; zinc; bis-triphenylphosphine-palladium(II) chloride; In diethyl ether; dichloromethane;
DOI:10.1002/hlca.200390315

Reference yield:

: 652153-15-6
(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-ol trifluoronethanesulfonate

: 652153-18-9
(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid 1,1-dimethylethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 83 percent / K₂CO₃; LiCl; 1-methylpyrrolidin-2-one / dichlorobis(triphenylphosphine)palladium / 24 h / 130 °C / 10343 Torr

2.1: 86 percent / Dibal-H / CH₂Cl₂ / -78 °C

3.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

4.1: Zn; I₂ / diethyl ether / 2 h / 20 °C

4.2: 87 percent / diethyl ether / 3 h / 20 °C

5.1: 92 percent / Dess-Martin periodianne / CH₂Cl₂ / 0.75 h / 20 °C

With 1-methyl-pyrrolidin-2-one; iodine; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; lithium chloride; zinc; bis-triphenylphosphine-palladium(II) chloride; In diethyl ether; dichloromethane;
DOI:10.1002/hlca.200390315