(4aR,5R,8aR)-6-Formyl-1,4a-dimethyl-5-(4-methyl-3-oxo-pentyl)-1,2,3,4,4a,5,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Base Information

Chemical Name:(4aR,5R,8aR)-6-Formyl-1,4a-dimethyl-5-(4-methyl-3-oxo-pentyl)-1,2,3,4,4a,5,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester
CAS No.:82652-61-7
Molecular Formula:C₂₁H₃₂O₄
Molecular Weight:348.483
Hs Code.:

Synonyms:(4aR,5R,8aR)-6-Formyl-1,4a-dimethyl-5-(4-methyl-3-oxo-pentyl)-1,2,3,4,4a,5,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

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Chemical Property of (4aR,5R,8aR)-6-Formyl-1,4a-dimethyl-5-(4-methyl-3-oxo-pentyl)-1,2,3,4,4a,5,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

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Technology Process of (4aR,5R,8aR)-6-Formyl-1,4a-dimethyl-5-(4-methyl-3-oxo-pentyl)-1,2,3,4,4a,5,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

There total 1 articles about (4aR,5R,8aR)-6-Formyl-1,4a-dimethyl-5-(4-methyl-3-oxo-pentyl)-1,2,3,4,4a,5,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 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: 20.0%

: 22552-63-2
methyl 13β,14β-dihydroxyabieta-7-en-18-oate

: 1235-74-1,1757-97-7,2756-34-5,7151-00-0,10178-27-5,10178-29-7,21699-55-8,24035-60-7
Methyl dehydroabietate

: 17751-36-9
methyl 7-oxodehydroabietate

: 82652-61-7
(1R,4aR,5R,8aR)-methyl-6-formyl-1,4a-dimethyl-5-(4-methyl-3-oxopentyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate

Guidance literature:: With jones reagent; In acetone; at 0 ℃; for 0.5h;
DOI:10.1016/j.tet.2007.07.088

Reference yield:

: 82652-61-7
(4aR,5R,8aR)-6-Formyl-1,4a-dimethyl-5-(4-methyl-3-oxo-pentyl)-1,2,3,4,4a,5,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

: 6790-58-5
(-)-ambroxide

Guidance literature:: Multi-step reaction with 15 steps

1: 72 percent / p-TsOH / not given / Ambient temperature

2: 85 percent / Raney Ni (Wl) / ethanol; ethyl acetate

3: CH₂Cl₂ / -78 °C

4: 49 percent / O₃, / ethyl acetate; pyridine / -78 °C

5: 83 percent / LiAlH₄ / not given

7: propan-2-ol; xylene / 0 °C / Irradiation

8: 71 percent / OsO₄, tert-butyl-hydroperoxide, (Et)4NOH / acetone / 50 °C

10: Li-HMDS / tetrahydrofuran / Ambient temperature

11: 80 percent

13: mesitylenesulfonylchloride / pyridine

15: Li / various solvent(s)

With tert.-butylhydroperoxide; 2-mesitylenesulphonyl chloride; osmium(VIII) oxide; lithium aluminium tetrahydride; tetraethylammonium hydroxide; lithium; nickel; toluene-4-sulfonic acid; ozone; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; ethanol; dichloromethane; ethyl acetate; isopropyl alcohol; acetone; xylene;
DOI:10.1016/S0040-4039(00)96229-4

Reference yield:

: 82652-61-7
(1R,4aR,5R,8aR)-methyl-6-formyl-1,4a-dimethyl-5-(4-methyl-3-oxopentyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate

: 889112-24-7
methyl 14-(p-toluenesulfonate)abiet-13-one-19-oate

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / H₂O / Raney-Ni / tetrahydrofuran / 20 °C

2: 70 percent / pyridine / 4 h

With pyridine; water; nickel; In tetrahydrofuran;
DOI:10.1055/s-2006-926392