(1R,3aR,4R,7S,8S,8aR)-hexahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulene-8a(4H)-ol

Base Information

Chemical Name:(1R,3aR,4R,7S,8S,8aR)-hexahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulene-8a(4H)-ol
CAS No.:533928-93-7
Molecular Formula:C₂₂H₃₂O₂
Molecular Weight:328.495
Hs Code.:

Synonyms:(1R,3aR,4R,7S,8S,8aR)-hexahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulene-8a(4H)-ol

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Chemical Property of (1R,3aR,4R,7S,8S,8aR)-hexahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulene-8a(4H)-ol

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Technology Process of (1R,3aR,4R,7S,8S,8aR)-hexahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulene-8a(4H)-ol

There total 3 articles about (1R,3aR,4R,7S,8S,8aR)-hexahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulene-8a(4H)-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: 74.0%

: (1S,2S,4R)-4,8,11,11-tetramethyl-2-(phenylmethoxy)-bicyclo[5.3.1]undec-7⁽⁸⁾-en-3-one

: 533928-93-7
(1R,3aR,4R,7S,8S,8aR)-hexahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulene-8a(4H)-ol

Guidance literature:: With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; thiophenol; In tetrahydrofuran; at 0 ℃;
DOI:10.1039/b206372g

Reference yield:

: 210633-78-6
(1R,3S,4S)-1,5,5-trimethyl-6-methylene-3-(phenylmethoxy)bicyclo[2.2.2]octan-2-one

: 533928-93-7
(1R,3aR,4R,7S,8S,8aR)-hexahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulene-8a(4H)-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: tert-butyllithium / diethyl ether; pentane / 0.25 h / -78 °C

1.2: 89 percent / diethyl ether / 0.08 h / -78 °C

2.1: 86 percent / NaH / tetrahydrofuran / 3 h / Heating

3.1: 74 percent / PhSH; SmI₂; hexamethylphosphoramide / tetrahydrofuran / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; tert.-butyl lithium; sodium hydride; thiophenol; In tetrahydrofuran; diethyl ether; pentane;
DOI:10.1039/b206372g

Reference yield:

: 533928-91-5
(1R,2R,3S,4S)-3-Benzyloxy-2-isopropenyl-1,5,5-trimethyl-6-methylene-bicyclo[2.2.2]octan-2-ol

: 533928-93-7
(1R,3aR,4R,7S,8S,8aR)-hexahydro-1,4,9,9-tetramethyl-8-(phenylmethoxy)-1H-3a,7-methanoazulene-8a(4H)-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / NaH / tetrahydrofuran / 3 h / Heating

2: 74 percent / PhSH; SmI₂; hexamethylphosphoramide / tetrahydrofuran / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide; sodium hydride; thiophenol; In tetrahydrofuran;
DOI:10.1039/b206372g