(4R,4aS,8R,8aR)-4-[(1S)-2-(benzyloxy)-1-methylethyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-3,4,4a,7,8,8a-hexahydro-6-methyl-2(1H)-naphthalenone

Base Information

Chemical Name:(4R,4aS,8R,8aR)-4-[(1S)-2-(benzyloxy)-1-methylethyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-3,4,4a,7,8,8a-hexahydro-6-methyl-2(1H)-naphthalenone
CAS No.:583866-68-6
Molecular Formula:C₃₂H₅₂O₃Si
Molecular Weight:512.849
Hs Code.:

(4R,4aS,8R,8aR)-4-[(1S)-2-(benzyloxy)-1-methylethyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-3,4,4a,7,8,8a-hexahydro-6-methyl-2(1H)-naphthalenone

Synonyms:(4R,4aS,8R,8aR)-4-[(1S)-2-(benzyloxy)-1-methylethyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-3,4,4a,7,8,8a-hexahydro-6-methyl-2(1H)-naphthalenone

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Chemical Property of (4R,4aS,8R,8aR)-4-[(1S)-2-(benzyloxy)-1-methylethyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-3,4,4a,7,8,8a-hexahydro-6-methyl-2(1H)-naphthalenone

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Technology Process of (4R,4aS,8R,8aR)-4-[(1S)-2-(benzyloxy)-1-methylethyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-3,4,4a,7,8,8a-hexahydro-6-methyl-2(1H)-naphthalenone

There total 4 articles about (4R,4aS,8R,8aR)-4-[(1S)-2-(benzyloxy)-1-methylethyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-3,4,4a,7,8,8a-hexahydro-6-methyl-2(1H)-naphthalenone 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: 73.0%

: 583866-52-8
(1S,2S,4S,8R)-2-[(1E,3S)-4-(benzyloxy)-3-methyl-1-butenyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-1-methylbicyclo[2.2.2]oct-5-en-2-ol

: 583866-68-6
(4R,4aS,8R,8aR)-4-[(1S)-2-(benzyloxy)-1-methylethyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-3,4,4a,7,8,8a-hexahydro-6-methyl-2(1H)-naphthalenone

Guidance literature:: With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 100 - 110 ℃; for 3h;
DOI:10.1021/jo0301301

Reference yield:

: 583865-95-6
(1S,4S,8R)-8-[(R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-1-methylbicyclo[2.2.2]oct-5-en-2-one

: 583866-68-6
(4R,4aS,8R,8aR)-4-[(1S)-2-(benzyloxy)-1-methylethyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-3,4,4a,7,8,8a-hexahydro-6-methyl-2(1H)-naphthalenone

Guidance literature:: Multi-step reaction with 2 steps

1.1: tert-butyllithium / tetrahydrofuran; pentane / 0.08 h / -78 °C

1.2: 16 percent / tetrahydrofuran; pentane / 0.5 h / -78 °C

2.1: 73 percent / 18-crown-6; potassium hexamethyldisilazide / tetrahydrofuran; toluene / 3 h / 100 - 110 °C

With 18-crown-6 ether; tert.-butyl lithium; potassium hexamethylsilazane; In tetrahydrofuran; toluene; pentane;
DOI:10.1021/jo0301301

Reference yield:

: 4-[(R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-6-methyl-2-cyclohexen-1-one

: 583866-68-6
(4R,4aS,8R,8aR)-4-[(1S)-2-(benzyloxy)-1-methylethyl]-8-[(1R)-1-[(tert-butyldimethylsiloxy)methyl]-2-methylpropyl]-3,4,4a,7,8,8a-hexahydro-6-methyl-2(1H)-naphthalenone

Guidance literature:: Multi-step reaction with 3 steps

1.1: hexamethyldisilazane; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

1.2: tetrahydrofuran; hexane / 3 h / 3 - 6 °C

1.3: 1.16 g / calcium carbonate / toluene / 24 h / Heating

2.1: tert-butyllithium / tetrahydrofuran; pentane / 0.08 h / -78 °C

2.2: 16 percent / tetrahydrofuran; pentane / 0.5 h / -78 °C

3.1: 73 percent / 18-crown-6; potassium hexamethyldisilazide / tetrahydrofuran; toluene / 3 h / 100 - 110 °C

With n-butyllithium; 18-crown-6 ether; tert.-butyl lithium; potassium hexamethylsilazane; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; toluene; pentane; 1.2: Michael reaction;
DOI:10.1021/jo0301301