(1R,2R,4aS,6R,8R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-hydroxy-1-(<(R)-(O-methylmandelyl)oxy>methyl)naphthalene

Base Information

Chemical Name:(1R,2R,4aS,6R,8R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-hydroxy-1-(<(R)-(O-methylmandelyl)oxy>methyl)naphthalene
CAS No.:101761-31-3
Molecular Formula:C₂₂H₃₀O₄
Molecular Weight:358.478
Hs Code.:

Synonyms:(1R,2R,4aS,6R,8R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-hydroxy-1-(<(R)-(O-methylmandelyl)oxy>methyl)naphthalene

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Chemical Property of (1R,2R,4aS,6R,8R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-hydroxy-1-(<(R)-(O-methylmandelyl)oxy>methyl)naphthalene

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Technology Process of (1R,2R,4aS,6R,8R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-hydroxy-1-(<(R)-(O-methylmandelyl)oxy>methyl)naphthalene

There total 12 articles about (1R,2R,4aS,6R,8R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-hydroxy-1-(<(R)-(O-methylmandelyl)oxy>methyl)naphthalene 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:

: 101761-22-2
(1RS,2SR,6SR,8SR,8aRS)-1,2,3,5,6,7,8,8a-octahydro-2,6-dimethyl-1-ethynyl-8-hydroxynaphthalene

: 101761-31-3
(1R,2R,4aS,6R,8R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-hydroxy-1-(<(R)-(O-methylmandelyl)oxy>methyl)naphthalene

Guidance literature:: Multi-step reaction with 10 steps

1: 99 percent / quinoline, hydrogen / Pd/BaSO₄ / 50 h

2: 92 percent / 4-(dimethylamino)pyridine / pyridine / 7 h / 60 °C / Heating

3: 95 percent / m-PCBA / CH₂Cl₂ / 1 h / 0 °C

4: 100 percent / boron trifluoride etherate / benzene / 11 h / Ambient temperature

5: 85 percent / ozone, dimethyl sulfide / CH₂Cl₂ / 18 h / 40 °C / Heating

6: 91 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

7: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C

8: 85 percent / HCl / methanol / 15 h / 0 °C

9: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min

10: DMAP, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 0 °C

With quinoline; hydrogenchloride; dmap; potassium hydroxide; dimethylsulfide; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; methyllithium; hydrogen; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; Pd-BaSO₄; In tetrahydrofuran; pyridine; methanol; dichloromethane; benzene;
DOI:10.1021/ja00275a053

Reference yield:

: 99342-52-6
(3aRS,4SR,8SR,9aSR,9bRS)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-3-oxo-4,8-dimethylnaphtho<1,8-bc>pyran

: 101761-31-3
(1R,2R,4aS,6R,8R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-hydroxy-1-(<(R)-(O-methylmandelyl)oxy>methyl)naphthalene

Guidance literature:: Multi-step reaction with 12 steps

1: 94 percent / methanol / 18 h / Ambient temperature

2: 86 percent / n-BuLi / hexane; diethyl ether; tetrahydrofuran / 1 h / 2 °C

3: 99 percent / quinoline, hydrogen / Pd/BaSO₄ / 50 h

4: 92 percent / 4-(dimethylamino)pyridine / pyridine / 7 h / 60 °C / Heating

5: 95 percent / m-PCBA / CH₂Cl₂ / 1 h / 0 °C

6: 100 percent / boron trifluoride etherate / benzene / 11 h / Ambient temperature

7: 85 percent / ozone, dimethyl sulfide / CH₂Cl₂ / 18 h / 40 °C / Heating

8: 91 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

9: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C

10: 85 percent / HCl / methanol / 15 h / 0 °C

11: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min

12: DMAP, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 0 °C

With quinoline; hydrogenchloride; dmap; potassium hydroxide; n-butyllithium; dimethylsulfide; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; methyllithium; hydrogen; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; Pd-BaSO₄; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/ja00275a053

Reference yield:

: 101773-26-6
(3aRS,4SR,8SR,9aSR,9bRS)-2,3,3a,4,5,7,8,9,9a,9b-decahydro-4,8-dimethyl-3-oxonaphtho<1,8-bc>pyran p-toluenesulfonylhydrazone

: 101761-31-3
(1R,2R,4aS,6R,8R,8aR)-1,2,4a,5,6,7,8,8a-octahydro-2,6-dimethyl-8-hydroxy-1-(<(R)-(O-methylmandelyl)oxy>methyl)naphthalene

Guidance literature:: Multi-step reaction with 11 steps

1: 86 percent / n-BuLi / hexane; diethyl ether; tetrahydrofuran / 1 h / 2 °C

2: 99 percent / quinoline, hydrogen / Pd/BaSO₄ / 50 h

3: 92 percent / 4-(dimethylamino)pyridine / pyridine / 7 h / 60 °C / Heating

4: 95 percent / m-PCBA / CH₂Cl₂ / 1 h / 0 °C

5: 100 percent / boron trifluoride etherate / benzene / 11 h / Ambient temperature

6: 85 percent / ozone, dimethyl sulfide / CH₂Cl₂ / 18 h / 40 °C / Heating

7: 91 percent / DBU / CH₂Cl₂ / 1 h / Ambient temperature

8: 93 percent / Li(t-BuO)3AlH / tetrahydrofuran / -78 °C

9: 85 percent / HCl / methanol / 15 h / 0 °C

10: 1.) MeLi, TMEDA; 2.) KOH / 1.) diethyl ether, 0 deg C, 10 min; 2.) methanol, 15 min

11: DMAP, 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 0 °C

With quinoline; hydrogenchloride; dmap; potassium hydroxide; n-butyllithium; dimethylsulfide; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; methyllithium; hydrogen; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; Pd-BaSO₄; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/ja00275a053