(Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one

Base Information

Chemical Name:(Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one
CAS No.:200860-11-3
Molecular Formula:C₃₀H₄₂O₇
Molecular Weight:514.659
Hs Code.:

Synonyms:(Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one

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Chemical Property of (Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one

There total 8 articles about (Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-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: 70.0%

: 200860-06-6
(Z)-(1S,2R,4S,5S,8R)-8-Hydroxy-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]undec-6-en-3-one

: 200860-11-3
(Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one

Guidance literature:: With pyridinium p-toluenesulfonate; In tert-butyl alcohol; for 48h; Heating;
DOI:10.1021/jo971591n

Reference yield:

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

: 200860-11-3
(Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one

Guidance literature:: Multi-step reaction with 8 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: 77 percent / lithium aluminum hydride / diethyl ether / 2 h

6: 86 percent / potassium carbonate / methanol / 0.5 h / Ambient temperature

7: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

8: 70 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 48 h / Heating

With lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; In methanol; diethyl ether; dichloromethane; tert-butyl alcohol;
DOI:10.1021/jo971591n

Reference yield:

: 200860-05-5
(Z)-(1R,4S,5S,6S,7R,8S)-4-{(S)-4-[(R)-1-(4-Methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-7-methoxymethoxy-5,11,11-trimethyl-bicyclo[6.2.1]undec-2-ene-1,6-diol

: 200860-11-3
(Z)-(1S,2R,4S,5S,8R)-2,8-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,11,11-trimethyl-bicyclo[6.2.1]undec-6-en-3-one

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

2: 70 percent / pyridinium p-toluenesulfonate / 2-methyl-propan-2-ol / 48 h / Heating

With pyridinium p-toluenesulfonate; Dess-Martin periodane; In dichloromethane; tert-butyl alcohol;
DOI:10.1021/jo971591n