1,2,4a,5,6,7,8,8aα-octahydro-7β-(benzyloxy)-2α-hydroxy-4aβ,8α-dimethylnaphthalene-3-carboxaldehyde

Base Information

Chemical Name:1,2,4a,5,6,7,8,8aα-octahydro-7β-(benzyloxy)-2α-hydroxy-4aβ,8α-dimethylnaphthalene-3-carboxaldehyde
CAS No.:84132-48-9
Molecular Formula:C₂₂H₃₀O₄
Molecular Weight:358.478
Hs Code.:

Synonyms:1,2,4a,5,6,7,8,8aα-octahydro-7β-(benzyloxy)-2α-hydroxy-4aβ,8α-dimethylnaphthalene-3-carboxaldehyde

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Chemical Property of 1,2,4a,5,6,7,8,8aα-octahydro-7β-(benzyloxy)-2α-hydroxy-4aβ,8α-dimethylnaphthalene-3-carboxaldehyde

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Technology Process of 1,2,4a,5,6,7,8,8aα-octahydro-7β-(benzyloxy)-2α-hydroxy-4aβ,8α-dimethylnaphthalene-3-carboxaldehyde

There total 8 articles about 1,2,4a,5,6,7,8,8aα-octahydro-7β-(benzyloxy)-2α-hydroxy-4aβ,8α-dimethylnaphthalene-3-carboxaldehyde 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: 55.0%

: 84132-47-8
(4aS,7S,8S,8aS)-7-Benzyloxy-3-[1,3]dioxolan-2-yl-4a,8-dimethyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

: 84132-49-0
1,2,4a,5,6,7,8,8aα-octahydro-7β-(benzyloxy)-2β-hydroxy-4aβ,8α-dimethylnaphthalene-3-carboxaldehyde

: 84132-48-9
1,2,4a,5,6,7,8,8aα-octahydro-7β-(benzyloxy)-2α-hydroxy-4aβ,8α-dimethylnaphthalene-3-carboxaldehyde

Guidance literature:: With L-Selectride; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/jo00152a012

Reference yield:

: 65898-63-7
3',4',4'a,5',6',7'-hexahydro-4'a,8-dimethylspiro<1,3-dioxolane-2,2'(1'H)-naphthalene>

: 84132-48-9
1,2,4a,5,6,7,8,8aα-octahydro-7β-(benzyloxy)-2α-hydroxy-4aβ,8α-dimethylnaphthalene-3-carboxaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: 63 percent / chromium trioxide - dipyridine complex / CH₂Cl₂

2: 69 percent / liq. NH₃, Li / ethanol; tetrahydrofuran

3: 71 percent / NaH / tetrahydrofuran

4: 89 percent / aq. HCl, AcOH / tetrahydrofuran

5: 93 percent / sodium methoxide

6: 64 percent / DDQ

7: 85 percent / p-TsOH / 3.5 h / 25 °C

8: 55 percent / L-Selectride / tetrahydrofuran / 2 h / 0 °C

With hydrogenchloride; 2,2'-bipyridine-chromium(VI) oxide; ammonia; sodium methylate; lithium; L-Selectride; sodium hydride; toluene-4-sulfonic acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jo00152a012

Reference yield:

: 84132-42-3
3',4',4'a,5',6',7',8',8'aα-octahydro-4'aβ,8'α-dimethylspiro-<1,3-dioxolane-2,2'(1'H)-naphthalen-7'β-ol>

: 84132-48-9
1,2,4a,5,6,7,8,8aα-octahydro-7β-(benzyloxy)-2α-hydroxy-4aβ,8α-dimethylnaphthalene-3-carboxaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 71 percent / NaH / tetrahydrofuran

2: 89 percent / aq. HCl, AcOH / tetrahydrofuran

3: 93 percent / sodium methoxide

4: 64 percent / DDQ

5: 85 percent / p-TsOH / 3.5 h / 25 °C

6: 55 percent / L-Selectride / tetrahydrofuran / 2 h / 0 °C

With hydrogenchloride; sodium methylate; L-Selectride; sodium hydride; toluene-4-sulfonic acid; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran;
DOI:10.1021/jo00152a012