(5E,7E)-(1S,2R,4S)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undeca-5,7-dien-3-one

Base Information

Chemical Name:(5E,7E)-(1S,2R,4S)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undeca-5,7-dien-3-one
CAS No.:200860-00-0
Molecular Formula:C₃₂H₄₄O₇
Molecular Weight:540.697
Hs Code.:

(5E,7E)-(1S,2R,4S)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undeca-5,7-dien-3-one

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Chemical Property of (5E,7E)-(1S,2R,4S)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undeca-5,7-dien-3-one

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Technology Process of (5E,7E)-(1S,2R,4S)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undeca-5,7-dien-3-one

There total 5 articles about (5E,7E)-(1S,2R,4S)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undeca-5,7-dien-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:

: 162790-67-2
(1R,3R,4S)-3-Methoxymethoxy-7,7-dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carbaldehyde

: 200860-00-0
(5E,7E)-(1S,2R,4S)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undeca-5,7-dien-3-one

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) potassium hexamethyldisilazide / 1.) toluene, THF, 0 deg C, 30 min, 2.) THF, toluene, 2 h

2: 1.) n-butyllithium / 1.) ether, hexanes, -78 deg C, 1 min, 2.) ether, hexanes, -78 deg C, 2 min

3: 1.) 18-crown-6, potassium hexamethyldisilazide / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 1 h

4: 91 percent / m-chloroperbenzoic acid, sodium bicarbonate / CH₂Cl₂ / 0.17 h / -78 °C

5: 374 mg / tetrahydrofuran / 3 h / Heating

With n-butyllithium; 18-crown-6 ether; potassium hexamethylsilazane; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo971591n

Reference yield:

: 200859-97-8
(1S,2S,3R,4S)-2-((Z)-2-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-vinyl)-3-methoxymethoxy-7,7-dimethyl-1-((Z)-2-phenylsulfanyl-vinyl)-bicyclo[2.2.1]heptan-2-ol

: 200860-00-0
(5E,7E)-(1S,2R,4S)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undeca-5,7-dien-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) 18-crown-6, potassium hexamethyldisilazide / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 1 h

2: 91 percent / m-chloroperbenzoic acid, sodium bicarbonate / CH₂Cl₂ / 0.17 h / -78 °C

3: 374 mg / tetrahydrofuran / 3 h / Heating

With 18-crown-6 ether; potassium hexamethylsilazane; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo971591n

Reference yield:

: 200859-98-9
(E)-(1S,2R,4S,5S,6R)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-6-phenylsulfanyl-bicyclo[6.2.1]undec-7-en-3-one

: 200860-00-0
(5E,7E)-(1S,2R,4S)-5-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-methoxymethoxy-4,11,11-trimethyl-bicyclo[6.2.1]undeca-5,7-dien-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / m-chloroperbenzoic acid, sodium bicarbonate / CH₂Cl₂ / 0.17 h / -78 °C

2: 374 mg / tetrahydrofuran / 3 h / Heating

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo971591n