(2R,6R,8aR)-6-[1-(4-Methoxy-benzyloxymethyl)-vinyl]-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol

Base Information

Chemical Name:(2R,6R,8aR)-6-[1-(4-Methoxy-benzyloxymethyl)-vinyl]-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol
CAS No.:140185-04-2
Molecular Formula:C₂₃H₃₂O₃
Molecular Weight:356.505
Hs Code.:

Synonyms:(2R,6R,8aR)-6-[1-(4-Methoxy-benzyloxymethyl)-vinyl]-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol

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Chemical Property of (2R,6R,8aR)-6-[1-(4-Methoxy-benzyloxymethyl)-vinyl]-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol

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Technology Process of (2R,6R,8aR)-6-[1-(4-Methoxy-benzyloxymethyl)-vinyl]-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol

There total 14 articles about (2R,6R,8aR)-6-[1-(4-Methoxy-benzyloxymethyl)-vinyl]-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol 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: 88.7%

: 140185-03-1
tert-Butoxy-{(2R,6R,8aR)-6-[1-(4-methoxy-benzyloxymethyl)-vinyl]-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-yloxy}-diphenyl-silane

: 140185-04-2
(2R,6R,8aR)-6-[1-(4-Methoxy-benzyloxymethyl)-vinyl]-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;

Reference yield:

: 21683-08-9
(1R,4aR,7R,8aR)-8a-hydroxy-1,4a-dimethyl-7-(prop-1-en-2-yl)-octahydronaphthalen-2(1H)-one

: 140185-04-2
(2R,6R,8aR)-6-[1-(4-Methoxy-benzyloxymethyl)-vinyl]-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol

Guidance literature:: Multi-step reaction with 14 steps

1: 79.2 percent / lithium aluminum hydride / tetrahydrofuran

2: 93.9 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

3: 95.3 percent / 80 percent m-chloroperbenzoic acid / CHCl₃ / 1 h / 0 - 5 °C

4: 88.2 percent / lithium diethylamide / diethyl ether / 8 h / Heating

5: 1. NaH / 1.) DMF, 2.) room temperature, 4 h

6: pyridinium p-toluenesulfonate / ethanol / 4 h / 70 °C

7: Jones reagent / acetone / 0 °C

8: 98.1 percent / KOH / methanol / 6 h / Heating

9: 1.) K naphthalenide, hexamethyldisilazane, 2.) 2-benzenesulfonyl-3-phenyloxaziridine / 1.) THF, -78 deg C, 30 min, 2.) THF, 2 h

10: 59 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 5 h / 0 °C

11: 39.9 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / -78 °C

13: 95.6 percent / tri-n-butyltin hydride, 2,2'-azobisisobutyronitrile / toluene / 2 h / Heating

14: 88.7 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

With dmap; potassium hydroxide; lithium aluminium tetrahydride; jones reagent; 2,2'-azobis(isobutyronitrile); lithium diethylamide; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; potassium naphthalene anion radical; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; acetone; toluene;

Reference yield:

: 140184-90-3,73839-11-9
10-epieudesm-11-ene-3β,5α-diol

: 140185-04-2
(2R,6R,8aR)-6-[1-(4-Methoxy-benzyloxymethyl)-vinyl]-4,8a-dimethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-2-ol

Guidance literature:: Multi-step reaction with 13 steps

1: 93.9 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / Ambient temperature

2: 95.3 percent / 80 percent m-chloroperbenzoic acid / CHCl₃ / 1 h / 0 - 5 °C

3: 88.2 percent / lithium diethylamide / diethyl ether / 8 h / Heating

4: 1. NaH / 1.) DMF, 2.) room temperature, 4 h

5: pyridinium p-toluenesulfonate / ethanol / 4 h / 70 °C

6: Jones reagent / acetone / 0 °C

7: 98.1 percent / KOH / methanol / 6 h / Heating

8: 1.) K naphthalenide, hexamethyldisilazane, 2.) 2-benzenesulfonyl-3-phenyloxaziridine / 1.) THF, -78 deg C, 30 min, 2.) THF, 2 h

9: 59 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 5 h / 0 °C

10: 39.9 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / -78 °C

12: 95.6 percent / tri-n-butyltin hydride, 2,2'-azobisisobutyronitrile / toluene / 2 h / Heating

13: 88.7 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

With dmap; potassium hydroxide; lithium aluminium tetrahydride; jones reagent; 2,2'-azobis(isobutyronitrile); lithium diethylamide; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; potassium naphthalene anion radical; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; acetone; toluene;