(Z)-(1S,2R,4R,5S,8R)-4,8-Dihydroxy-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

Base Information

Chemical Name:(Z)-(1S,2R,4R,5S,8R)-4,8-Dihydroxy-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
CAS No.:200860-07-7
Molecular Formula:C₃₂H₄₆O₉
Molecular Weight:574.712
Hs Code.:

(Z)-(1S,2R,4R,5S,8R)-4,8-Dihydroxy-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

Synonyms:(Z)-(1S,2R,4R,5S,8R)-4,8-Dihydroxy-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

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Chemical Property of (Z)-(1S,2R,4R,5S,8R)-4,8-Dihydroxy-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

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Technology Process of (Z)-(1S,2R,4R,5S,8R)-4,8-Dihydroxy-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

There total 9 articles about (Z)-(1S,2R,4R,5S,8R)-4,8-Dihydroxy-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 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: 66.0%

: 40949-94-8
potassium hexamethylsilazane

: 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

: 200860-07-7
(Z)-(1S,2R,4R,5S,8R)-4,8-Dihydroxy-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

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

Guidance literature:: With 18-crown-6 ether; oxygen; In tetrahydrofuran; toluene; for 0.333333h;
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

: 200860-07-7
(Z)-(1S,2R,4R,5S,8R)-4,8-Dihydroxy-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

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: 66 percent / 18-crown-6, oxygen / tetrahydrofuran; toluene / 0.33 h

With lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; oxygen; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
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

: 200860-07-7
(Z)-(1S,2R,4R,5S,8R)-4,8-Dihydroxy-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

Guidance literature:: Multi-step reaction with 2 steps

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

2: 66 percent / 18-crown-6, oxygen / tetrahydrofuran; toluene / 0.33 h

With 18-crown-6 ether; oxygen; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo971591n