(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

Base Information

Chemical Name:(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
CAS No.:200860-05-5
Molecular Formula:C₃₂H₄₈O₈
Molecular Weight:560.728
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 6 articles about (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 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: 86.0%

: 200860-04-4
Trifluoro-acetic acid (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-6-(2,2,2-trifluoro-acetoxy)-bicyclo[6.2.1]undec-2-en-1-yl ester

: 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

Guidance literature:: With potassium carbonate; In methanol; for 0.5h; Ambient temperature;
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

: 200860-05-5
(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

Guidance literature:: Multi-step reaction with 6 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

With lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; potassium hexamethylsilazane; potassium carbonate; In methanol; diethyl ether;
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

: 200860-05-5
(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

Guidance literature:: Multi-step reaction with 4 steps

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

2: 77 percent / lithium aluminum hydride / diethyl ether / 2 h

4: 86 percent / potassium carbonate / methanol / 0.5 h / Ambient temperature

With lithium aluminium tetrahydride; 18-crown-6 ether; potassium hexamethylsilazane; potassium carbonate; In methanol; diethyl ether;
DOI:10.1021/jo971591n