(4aS,5R,6S,8aR)-5-(6-Hydroxy-2,3-dimethoxy-benzyl)-5,6,8a-trimethyl-octahydro-naphthalen-1-one

Base Information

Chemical Name:(4aS,5R,6S,8aR)-5-(6-Hydroxy-2,3-dimethoxy-benzyl)-5,6,8a-trimethyl-octahydro-naphthalen-1-one
CAS No.:363139-97-3
Molecular Formula:C₂₂H₃₂O₄
Molecular Weight:360.494
Hs Code.:

Synonyms:(4aS,5R,6S,8aR)-5-(6-Hydroxy-2,3-dimethoxy-benzyl)-5,6,8a-trimethyl-octahydro-naphthalen-1-one

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Chemical Property of (4aS,5R,6S,8aR)-5-(6-Hydroxy-2,3-dimethoxy-benzyl)-5,6,8a-trimethyl-octahydro-naphthalen-1-one

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Technology Process of (4aS,5R,6S,8aR)-5-(6-Hydroxy-2,3-dimethoxy-benzyl)-5,6,8a-trimethyl-octahydro-naphthalen-1-one

There total 19 articles about (4aS,5R,6S,8aR)-5-(6-Hydroxy-2,3-dimethoxy-benzyl)-5,6,8a-trimethyl-octahydro-naphthalen-1-one 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: 98.0%

: 363139-96-2
C₁₆H₂₆O₃C₁₀H₁₄O₃

: 363139-97-3
(4aS,5R,6S,8aR)-5-(6-Hydroxy-2,3-dimethoxy-benzyl)-5,6,8a-trimethyl-octahydro-naphthalen-1-one

Guidance literature:: With hydrogenchloride; In methanol; at 40 ℃; for 2.5h;
DOI:10.1021/ol016285h

Reference yield:

: 2033-89-8
3,4-dimethoxyphenol

: 363139-97-3
(4aS,5R,6S,8aR)-5-(6-Hydroxy-2,3-dimethoxy-benzyl)-5,6,8a-trimethyl-octahydro-naphthalen-1-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 78 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / 0 - 20 °C

2.1: N,N,N',N'-tetramethylethylenediamine / pentane; diethyl ether / 1 h / -78 °C

2.2: bromine / pentane; diethyl ether / 3 h / -78 - 0 °C

2.3: hydrochlorid acid / H₂O; methanol / 5 h / 40 °C

3.1: 96 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -40 °C

4.2: 97 percent / tetrahydrofuran; hexane / 2 h / -40 - -20 °C

5.1: NaN(TMS)2 / tetrahydrofuran / 0.5 h / -78 °C

5.2: tetrahydrofuran / 1 h / -78 - -55 °C

5.3: 94 percent / tetrahydrofuran / 2 h / -78 - -55 °C

6.1: 77 percent / n-Bu₃SnH; AIBN / toluene / 2 h / Heating

7.1: 98 percent / aq. HCl / methanol / 2.5 h / 40 °C

With hydrogenchloride; n-butyllithium; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; pentane;
DOI:10.1021/ol016285h

Reference yield:

: 133129-56-3
1,2-dimethoxy-4-(methoxymethoxy)benzene

: 363139-97-3
(4aS,5R,6S,8aR)-5-(6-Hydroxy-2,3-dimethoxy-benzyl)-5,6,8a-trimethyl-octahydro-naphthalen-1-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: N,N,N',N'-tetramethylethylenediamine / pentane; diethyl ether / 1 h / -78 °C

1.2: bromine / pentane; diethyl ether / 3 h / -78 - 0 °C

1.3: hydrochlorid acid / H₂O; methanol / 5 h / 40 °C

2.1: 96 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -40 °C

3.2: 97 percent / tetrahydrofuran; hexane / 2 h / -40 - -20 °C

4.1: NaN(TMS)2 / tetrahydrofuran / 0.5 h / -78 °C

4.2: tetrahydrofuran / 1 h / -78 - -55 °C

4.3: 94 percent / tetrahydrofuran / 2 h / -78 - -55 °C

5.1: 77 percent / n-Bu₃SnH; AIBN / toluene / 2 h / Heating

6.1: 98 percent / aq. HCl / methanol / 2.5 h / 40 °C

With hydrogenchloride; n-butyllithium; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; pentane;
DOI:10.1021/ol016285h