[(1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol

Base Information

Chemical Name:[(1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol
CAS No.:936368-43-3
Molecular Formula:C₂₇H₄₄O₄Si
Molecular Weight:460.729
Hs Code.:

Synonyms:[(1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol

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Chemical Property of [(1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol

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Technology Process of [(1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol

There total 7 articles about [(1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol 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:

: 936368-35-3
ethyl (1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

: 936368-43-3
[(1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -20 - 23 ℃;
DOI:10.1021/ol070049a

Reference yield:

: 936368-33-1
ethyl (2E,4S,6R,8E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6,9-dimethyl-10-oxodeca-2,8-dienoate

: 936368-43-3
[(1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

1.2: tetrahydrofuran / -80 - 0 °C

1.3: CHCl₃ / 2 h / 60 °C

2.1: 1.610 g / diisobutylaluminium hydride / CH₂Cl₂ / -20 - 23 °C

With potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol070049a

Reference yield:

: 936368-30-8
ethyl (2E,4S,6R)-8-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-6-methyloct-2-enoate

: 936368-43-3
[(1S,2S,4aS,6R,8S,8aS)-8-{[tert-butyl(dimethyl)silyl]oxy}-2-(3,5-dimethoxyphenyl)-4,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]methanol

Guidance literature:: Multi-step reaction with 6 steps

1.1: imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 14 h / 0 - 23 °C

2.1: camphorsulfonic acid / methanol / 1 h / 20 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4.1: toluene / 30 h / 100 °C

5.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

5.2: tetrahydrofuran / -80 - 0 °C

5.3: CHCl₃ / 2 h / 60 °C

6.1: 1.610 g / diisobutylaluminium hydride / CH₂Cl₂ / -20 - 23 °C

With 1H-imidazole; dmap; camphor-10-sulfonic acid; potassium tert-butylate; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; toluene; 3.1: Dess-Martin oxidation / 4.1: Wittig reaction;
DOI:10.1021/ol070049a