(4RS,4aRS,5SR,7SR,8RS,8aSR)-4,5,7-trimethyl-8-(benzyloxy)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-4-carboxaldehyde

Base Information

Chemical Name:(4RS,4aRS,5SR,7SR,8RS,8aSR)-4,5,7-trimethyl-8-(benzyloxy)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-4-carboxaldehyde
CAS No.:101032-67-1
Molecular Formula:C₂₁H₂₈O₂
Molecular Weight:312.452
Hs Code.:

Synonyms:(4RS,4aRS,5SR,7SR,8RS,8aSR)-4,5,7-trimethyl-8-(benzyloxy)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-4-carboxaldehyde

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Chemical Property of (4RS,4aRS,5SR,7SR,8RS,8aSR)-4,5,7-trimethyl-8-(benzyloxy)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-4-carboxaldehyde

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Technology Process of (4RS,4aRS,5SR,7SR,8RS,8aSR)-4,5,7-trimethyl-8-(benzyloxy)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-4-carboxaldehyde

There total 13 articles about (4RS,4aRS,5SR,7SR,8RS,8aSR)-4,5,7-trimethyl-8-(benzyloxy)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-4-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:

: (2E,4RS,6RS,8E)-2,4,6-trimethyl-7-(benzyloxy)-2,8,10-undecatrienal

: 101032-67-1
(4RS,4aRS,5SR,7SR,8RS,8aSR)-4,5,7-trimethyl-8-(benzyloxy)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-4-carboxaldehyde

: 101032-66-0
(4RS,4aRS,5SR,7SR,8SR,8aSR)-4,5,7-trimethyl-8-(benzyloxy)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-4-carboxaldehyde

Guidance literature:: With dimethylaluminum chloride; In hexane; dichloromethane; at -13 ℃; for 12h; Title compound not separated from byproducts;
DOI:10.1021/ja00238a030

Reference yield:

: 54630-82-9
(2R^*,4R^*)-2,4-dimethyl-1,5-pentanediol

: 101032-67-1
(4RS,4aRS,5SR,7SR,8RS,8aSR)-4,5,7-trimethyl-8-(benzyloxy)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-4-carboxaldehyde

Guidance literature:: Multi-step reaction with 11 steps

1: 42 percent / imidazole / dimethylformamide / 30 h / Ambient temperature

2: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 2) CH₂Cl₂, -60 to -25 deg C

3: 1) n-BuLi / 1) THF, xylene, hexane, -78 deg C, 2) THF, xylene, hexane, -78 deg C

4: Red-Al / toluene / 3 h

5: 1) n-BuLi / 1) THF, hexane, 2) THF, hexane, HMPA

6: (nBu)4NF / tetrahydrofuran

7: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 2) CH₂Cl₂, -60 to -25 deg C

8: 98 percent / CH₂Cl₂ / 23 °C

9: DIBAH / diethyl ether; hexane / 1 h / -78 °C

10: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 2) CH₂Cl₂, -60 to -25 deg C

11: (CH₃)2AlCl / CH₂Cl₂; hexane / 12 h / -13 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethylaluminum chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00238a030

Reference yield:

: 101032-57-9
(2RS,4RS)-5-(tert-butyldimethylsilyloxy)-2,4-dimethylpentan-1-ol

: 101032-67-1
(4RS,4aRS,5SR,7SR,8RS,8aSR)-4,5,7-trimethyl-8-(benzyloxy)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-4-carboxaldehyde

Guidance literature:: Multi-step reaction with 10 steps

1: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 2) CH₂Cl₂, -60 to -25 deg C

2: 1) n-BuLi / 1) THF, xylene, hexane, -78 deg C, 2) THF, xylene, hexane, -78 deg C

3: Red-Al / toluene / 3 h

4: 1) n-BuLi / 1) THF, hexane, 2) THF, hexane, HMPA

5: (nBu)4NF / tetrahydrofuran

6: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 2) CH₂Cl₂, -60 to -25 deg C

7: 98 percent / CH₂Cl₂ / 23 °C

8: DIBAH / diethyl ether; hexane / 1 h / -78 °C

9: 1) DMSO, (COCl)2, 2) Et₃N / 1) CH₂Cl₂, -60 deg C, 2) CH₂Cl₂, -60 to -25 deg C

10: (CH₃)2AlCl / CH₂Cl₂; hexane / 12 h / -13 °C

With n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethylaluminum chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/ja00238a030