(1S,2S,4S,5S,6R,8R,9S)-1,6-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-8-methoxymethoxy-6,12,12-trimethyl-3-oxa-tricyclo[7.2.1.0^2,4]dodecan-7-one

Base Information

• Chemical Name: (1S,2S,4S,5S,6R,8R,9S)-1,6-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-8-methoxymethoxy-6,12,12-trimethyl-3-oxa-tricyclo[7.2.1.0^2,4]dodecan-7-one
• CAS No.: 200860-09-9
• Molecular Formula: C₃₂H₄₆O₁₀
• Molecular Weight: 590.711

Synonyms:(1S,2S,4S,5S,6R,8R,9S)-1,6-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-8-methoxymethoxy-6,12,12-trimethyl-3-oxa-tricyclo[7.2.1.0^2,4]dodecan-7-one

Chemical Property of (1S,2S,4S,5S,6R,8R,9S)-1,6-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-8-methoxymethoxy-6,12,12-trimethyl-3-oxa-tricyclo[7.2.1.0^2,4]dodecan-7-one

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Technology Process of (1S,2S,4S,5S,6R,8R,9S)-1,6-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-8-methoxymethoxy-6,12,12-trimethyl-3-oxa-tricyclo[7.2.1.0^2,4]dodecan-7-one

There total 9 articles about (1S,2S,4S,5S,6R,8R,9S)-1,6-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-8-methoxymethoxy-6,12,12-trimethyl-3-oxa-tricyclo[7.2.1.0^2,4]dodecan-7-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: 96.0%

(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 (200860-07-7) → (1S,2S,4S,5S,6R,8R,9S)-1,6-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-8-methoxymethoxy-6,12,12-trimethyl-3-oxa-tricyclo[7.2.1.02,4]dodecan-7-one (200860-09-9)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 16h;

DOI:10.1021/jo971591n

Reference yield:

(1R,3R,4S)-3-Methoxymethoxy-7,7-dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-carbaldehyde (162790-67-2) → (1S,2S,4S,5S,6R,8R,9S)-1,6-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-8-methoxymethoxy-6,12,12-trimethyl-3-oxa-tricyclo[7.2.1.02,4]dodecan-7-one (200860-09-9)

Guidance literature:

Multi-step reaction with 9 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

9: 96 percent / m-chloroperbenzoic acid, sodium bicarbonate / CH₂Cl₂ / 16 h

With lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; oxygen; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jo971591n

Reference yield:

(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 (200860-05-5) → (1S,2S,4S,5S,6R,8R,9S)-1,6-Dihydroxy-5-{(S)-4-[(R)-1-(4-methoxy-benzyloxy)-allyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-8-methoxymethoxy-6,12,12-trimethyl-3-oxa-tricyclo[7.2.1.02,4]dodecan-7-one (200860-09-9)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 96 percent / m-chloroperbenzoic acid, sodium bicarbonate / CH₂Cl₂ / 16 h

With 18-crown-6 ether; oxygen; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo971591n

upstream raw materials:

(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

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

(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

(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

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