5β,8α-dibenzyloxy-2β-methyl-1β-<3-(1-ethoxyethoxy)propyl>-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene

Base Information

Chemical Name:5β,8α-dibenzyloxy-2β-methyl-1β-<3-(1-ethoxyethoxy)propyl>-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene
CAS No.:79782-48-2
Molecular Formula:C₃₂H₄₄O₄
Molecular Weight:492.699
Hs Code.:

Synonyms:5β,8α-dibenzyloxy-2β-methyl-1β-<3-(1-ethoxyethoxy)propyl>-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene

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Chemical Property of 5β,8α-dibenzyloxy-2β-methyl-1β-<3-(1-ethoxyethoxy)propyl>-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene

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Technology Process of 5β,8α-dibenzyloxy-2β-methyl-1β-<3-(1-ethoxyethoxy)propyl>-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene

There total 28 articles about 5β,8α-dibenzyloxy-2β-methyl-1β-<3-(1-ethoxyethoxy)propyl>-1,2,4aα,5,6,7,8,8aβ-octahydronaphthalene 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:

: 2906-93-6,3198-51-4,6102-42-7,36159-09-8,54963-84-7,84275-37-6
(+/-)-1,4,5,8,9,10-trans-hexahydronaphthalene-1,4-dione

: 79782-48-2
(1S,4S,4aR,5S,6S,8aR)-1,4-Bis-benzyloxy-5-[3-(1-ethoxy-ethoxy)-propyl]-6-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: Multi-step reaction with 14 steps

1: 33 percent / Aureobasidium pullulans NRRL Y-12610

2: 99 percent / NaH / dimethylsulfoxide / 25 °C

3: KOAc / 1 h / 25 °C

4: 89 percent / KOH / methanol; diethyl ether / 2 h / 25 °C

5: H₂O₂ / tetrahydrofuran / 2.5 h / 25 °C

6: 2 h / 55 °C

7: Jones reagent

8: 1.) THF, -20 deg C, 30 min, 2.) DME, -20 deg C, 15 min

9: THF, -78 deg C, 30 min

10: Et₃N / CH₂Cl₂ / 0.5 h / -5 °C

11: DBU / benzene / 25 °C

12: 81 percent / hydrogen, pyridine / Pd/C

13: ethanol / 7 h / 25 °C

14: LDA / tetrahydrofuran / -78 - 0 °C

With pyridine; potassium hydroxide; jones reagent; Aureobasidium pullulans NRRL Y-12610; hydrogen; dihydrogen peroxide; potassium acetate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.1021/ja00411a063

Reference yield:

: 84131-75-9
1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene

: 79782-48-2
(1S,4S,4aR,5S,6S,8aR)-1,4-Bis-benzyloxy-5-[3-(1-ethoxy-ethoxy)-propyl]-6-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: Multi-step reaction with 12 steps

1: KOAc / 1 h / 25 °C

2: 89 percent / KOH / methanol; diethyl ether / 2 h / 25 °C

3: H₂O₂ / tetrahydrofuran / 2.5 h / 25 °C

4: 2 h / 55 °C

5: Jones reagent

6: 1.) THF, -20 deg C, 30 min, 2.) DME, -20 deg C, 15 min

7: THF, -78 deg C, 30 min

8: Et₃N / CH₂Cl₂ / 0.5 h / -5 °C

9: DBU / benzene / 25 °C

10: 81 percent / hydrogen, pyridine / Pd/C

11: ethanol / 7 h / 25 °C

12: LDA / tetrahydrofuran / -78 - 0 °C

With pyridine; potassium hydroxide; jones reagent; hydrogen; dihydrogen peroxide; potassium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; benzene;
DOI:10.1021/ja00411a063

Reference yield:

: 84173-21-7
1β,4α-bis(benzyloxy)-7-oxo-1,2,3,4,4aβ,7,8,8aα-octahydronaphthalene

: 79782-48-2
(1S,4S,4aR,5S,6S,8aR)-1,4-Bis-benzyloxy-5-[3-(1-ethoxy-ethoxy)-propyl]-6-methyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) THF, -20 deg C, 30 min, 2.) DME, -20 deg C, 15 min

2: THF, -78 deg C, 30 min

3: Et₃N / CH₂Cl₂ / 0.5 h / -5 °C

4: DBU / benzene / 25 °C

5: 81 percent / hydrogen, pyridine / Pd/C

6: ethanol / 7 h / 25 °C

7: LDA / tetrahydrofuran / -78 - 0 °C

With pyridine; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; benzene;
DOI:10.1021/ja00411a063