(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol

Base Information

Chemical Name:(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol
CAS No.:113161-47-0
Molecular Formula:C₂₇H₃₄O₂
Molecular Weight:390.566
Hs Code.:

Synonyms:(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol

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Chemical Property of (4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol

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Technology Process of (4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol

There total 33 articles about (4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-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:

: (1S,2S,5S)-5-(1-hydroxypropan-2-yl)-2-methylcyclohexanol

: 113161-47-0
(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol

Guidance literature:: Multi-step reaction with 28 steps

1: pyridine

2: pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂

3: aq. KOH

4: pyridinium chlorochromate (PCC) , NaOAc / CH₂Cl₂

5: NaClO₂, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

6: aq. acetic acid / 80 °C

7: 67 percent / p-toluenesulfonic acid / toluene / Heating

8: lithium diisopropylamide (LDA) / hexamethylphosphoric acid triamide

9: H₂O₂

10: 79 percent / CuI, dimethyl sulfide, trimethylsilyl chloride / tetrahydrofuran / -40 °C

11: 84 percent / LiAlH₄ / tetrahydrofuran / 1 h / 25 °C

12: Et₃N, 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂

13: lithium triethylborohydride / tetrahydrofuran

14: pyridinium chlorochromate (PCC) / CH₂Cl₂

15: NaH / dioxane

16: Et₃N / hexane

17: 1.) TiCl₄, 2.) NaOMe / 1.) CH₂Cl₂, -78 deg C, 4 h, 2.) MeOH, 24 h

18: m-chloroperbenzoic acid (MCPBA), NaHCO₃ / CHCl₃ / 55 °C

19: SnCl₄ / CH₂Cl₂ / 20 °C

20: K₂CO₃ / dimethylsulfoxide

21: imidazole / dimethylformamide / 45 °C

22: diisopropylaluminum hydride (DIBAL) / CH₂Cl₂ / 20 °C

23: pyridinium chlorochromate (PCC) / CH₂Cl₂

24: m-chloroperbenzoic acid (MCPBA), Na₂HPO₄ / CHCl₃ / 3 h / 20 °C

25: tetrabutylammonium fluoride (TBAF), acetic acid / tetrahydrofuran

26: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 2.) CH₂Cl₂, -40 deg C

27: tetrahydrofuran / 0.5 h / 20 °C

28: (dimethylamino)formaldehyde dineopentyl acetal, 4,4-methylenebis(2,6-di-tert-butylphenol) / CHCl₃ / 72 h / 55 °C

With pyridine; 1H-imidazole; dmap; potassium hydroxide; sodium chlorite; disodium hydrogenphosphate; copper(l) iodide; lithium aluminium tetrahydride; chloro-trimethyl-silane; 2-methyl-but-2-ene; oxalyl dichloride; diisopropyl aluminum hydride; dimethylsulfide; 4,4'-Methylenebis(2,6-di-tert-butylphenol); tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; sodium acetate; pyridinium p-toluenesulfonate; titanium tetrachloride; tin(IV) chloride; sodium hydride; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; N,N-dimethylformamide dineopentyl acetal; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/jo00242a053

Reference yield:

: (1S,2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanol

: 113161-47-0
(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol

Guidance literature:: Multi-step reaction with 15 steps

1: pyridinium chlorochromate (PCC) / CH₂Cl₂

2: NaH / dioxane

3: Et₃N / hexane

4: 1.) TiCl₄, 2.) NaOMe / 1.) CH₂Cl₂, -78 deg C, 4 h, 2.) MeOH, 24 h

5: m-chloroperbenzoic acid (MCPBA), NaHCO₃ / CHCl₃ / 55 °C

6: SnCl₄ / CH₂Cl₂ / 20 °C

7: K₂CO₃ / dimethylsulfoxide

8: imidazole / dimethylformamide / 45 °C

9: diisopropylaluminum hydride (DIBAL) / CH₂Cl₂ / 20 °C

10: pyridinium chlorochromate (PCC) / CH₂Cl₂

11: m-chloroperbenzoic acid (MCPBA), Na₂HPO₄ / CHCl₃ / 3 h / 20 °C

12: tetrabutylammonium fluoride (TBAF), acetic acid / tetrahydrofuran

13: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 2.) CH₂Cl₂, -40 deg C

14: tetrahydrofuran / 0.5 h / 20 °C

15: (dimethylamino)formaldehyde dineopentyl acetal, 4,4-methylenebis(2,6-di-tert-butylphenol) / CHCl₃ / 72 h / 55 °C

With 1H-imidazole; disodium hydrogenphosphate; oxalyl dichloride; diisopropyl aluminum hydride; 4,4'-Methylenebis(2,6-di-tert-butylphenol); tetrabutyl ammonium fluoride; sodium methylate; titanium tetrachloride; tin(IV) chloride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; N,N-dimethylformamide dineopentyl acetal; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00242a053

Reference yield:

: 113161-41-4
(2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanone

: 113161-47-0
(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol

Guidance literature:: Multi-step reaction with 14 steps

1: NaH / dioxane

2: Et₃N / hexane

3: 1.) TiCl₄, 2.) NaOMe / 1.) CH₂Cl₂, -78 deg C, 4 h, 2.) MeOH, 24 h

4: m-chloroperbenzoic acid (MCPBA), NaHCO₃ / CHCl₃ / 55 °C

5: SnCl₄ / CH₂Cl₂ / 20 °C

6: K₂CO₃ / dimethylsulfoxide

7: imidazole / dimethylformamide / 45 °C

8: diisopropylaluminum hydride (DIBAL) / CH₂Cl₂ / 20 °C

9: pyridinium chlorochromate (PCC) / CH₂Cl₂

10: m-chloroperbenzoic acid (MCPBA), Na₂HPO₄ / CHCl₃ / 3 h / 20 °C

11: tetrabutylammonium fluoride (TBAF), acetic acid / tetrahydrofuran

12: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 2.) CH₂Cl₂, -40 deg C

13: tetrahydrofuran / 0.5 h / 20 °C

14: (dimethylamino)formaldehyde dineopentyl acetal, 4,4-methylenebis(2,6-di-tert-butylphenol) / CHCl₃ / 72 h / 55 °C

With 1H-imidazole; disodium hydrogenphosphate; oxalyl dichloride; diisopropyl aluminum hydride; 4,4'-Methylenebis(2,6-di-tert-butylphenol); tetrabutyl ammonium fluoride; sodium methylate; titanium tetrachloride; tin(IV) chloride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; N,N-dimethylformamide dineopentyl acetal; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00242a053