(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methoxy-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid prop-2-enyl ester

Base Information

Chemical Name:(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methoxy-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid prop-2-enyl ester
CAS No.:652153-13-4
Molecular Formula:C₂₄H₃₀O₄
Molecular Weight:382.5
Hs Code.:

Synonyms:(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methoxy-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid prop-2-enyl ester

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Chemical Property of (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methoxy-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid prop-2-enyl ester

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Technology Process of (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methoxy-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid prop-2-enyl ester

There total 13 articles about (4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methoxy-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid prop-2-enyl 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: 82.0%

: 107-18-6
allyl alcohol

: 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

: 652153-13-4
(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methoxy-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid prop-2-enyl ester

Guidance literature:: With dmap; In toluene; for 16h; Heating;
DOI:10.1002/hlca.200390315

Reference yield: 53.0%

: 63934-48-5
allyl cyanoformate

: 652153-20-3
1-[(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methyl-6-(phenylmethoxy)naphthalen-1-yl]ethanone

: 652153-13-4
(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methoxy-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid prop-2-enyl ester

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.25h;
DOI:10.1002/hlca.200390315

Reference yield:

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

: 652153-13-4
(4aR,6R,8aS)-3,4,4a,5,6,7,8,8a-octahydro-8a-methoxy-β-oxo-6-(phenylmethoxy)naphthalene-1-propanoic acid prop-2-enyl ester

Guidance literature:: Multi-step reaction with 7 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

7.1: 82 percent / DMAP / toluene / 16 h / Heating

With 1-methyl-pyrrolidin-2-one; dmap; 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; toluene;
DOI:10.1002/hlca.200390315