(E)-(1S,2R)-2-(4-Methoxy-benzyloxy)-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one

Base Information

Chemical Name:(E)-(1S,2R)-2-(4-Methoxy-benzyloxy)-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one
CAS No.:200704-88-7
Molecular Formula:C₂₃H₃₂O₃
Molecular Weight:356.505
Hs Code.:

Synonyms:(E)-(1S,2R)-2-(4-Methoxy-benzyloxy)-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one

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Chemical Property of (E)-(1S,2R)-2-(4-Methoxy-benzyloxy)-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one

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Technology Process of (E)-(1S,2R)-2-(4-Methoxy-benzyloxy)-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one

There total 1 articles about (E)-(1S,2R)-2-(4-Methoxy-benzyloxy)-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one 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:

: 200704-87-6
(1S,2S,3R,4S)-2-Isopropenyl-3-(4-methoxy-benzyloxy)-7,7-dimethyl-1-vinyl-bicyclo[2.2.1]heptan-2-ol

: 74-88-4
methyl iodide

: 200704-88-7
(E)-(1S,2R)-2-(4-Methoxy-benzyloxy)-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one

Guidance literature:: With 18-crown-6 ether; potassium hexamethylsilazane; Yield given. Multistep reaction; 1.) THF, toluene, -78 -> 0 deg C, 1 h, 2.) THF, toluene, -78 deg C, 1 h;
DOI:10.1021/jo971592f

Reference yield:

: 200704-88-7
(E)-(1S,2R)-2-(4-Methoxy-benzyloxy)-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one

: 200704-89-8
(E)-(1S,2R,3S)-2-(4-Methoxy-benzyloxy)-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-ol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 1h;
DOI:10.1021/jo971592f

Reference yield:

: 200704-88-7
(E)-(1S,2R)-2-(4-Methoxy-benzyloxy)-4,4,11,11-tetramethyl-bicyclo[6.2.1]undec-7-en-3-one

: Benzoic acid (1S,3R,6S,7R,8S)-7-(4-methoxy-benzyloxy)-6-(2-methoxy-ethoxymethoxy)-5,5,11,11-tetramethyl-2-oxo-1-(2-trimethylsilanyl-ethoxymethoxy)-bicyclo[6.2.1]undec-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: lithium aluminum hydride / diethyl ether / 1 h / 0 °C

2: 3.15 g / diisopropylethylamine, tetra-n-butylammonium iodide / dimethylformamide / 4 h / 60 °C

3: 1.) pyridine, osmium tetraoxide, 2.) NaHSO₃ / 1.) room temperature, 1.5 h, 2.) overnight

4: 1.) dimethyl sulfoxide, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, 0 deg C, 15 min

5: 79 percent / diisopropylethylamine / CH₂Cl₂ / 24 h / Ambient temperature

7: 38 mg / 4-(dimethylamino)pyridine / CH₂Cl₂

With pyridine; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; sodium hydrogensulfite; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo971592f