9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-3-ol

Base Information

Chemical Name:9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-3-ol
CAS No.:923275-80-3
Molecular Formula:C₂₉H₄₂O₅
Molecular Weight:470.649
Hs Code.:

9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2<i>H</i>-1-oxa-benzo[<i>cd</i>]cyclopenta[<i>h</i>]azulen-3-ol

Synonyms:9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-3-ol

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Chemical Property of 9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-3-ol

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Technology Process of 9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-3-ol

There total 13 articles about 9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-3-ol 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: 100.0%

: 923275-79-0
(9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-3-yloxy)-tert-butyl-diphenyl-silane

: 923275-80-3
9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-3-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1021/ja0660507

Reference yield:

: 627075-78-9
(E)-1-(4-Iodo-furan-3-yl)-4-methyl-hex-4-en-1-ol

: 923275-80-3
9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-3-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

2.1: (+)-B-chlorodiisopinocamphenylborane / tetrahydrofuran / -20 °C

3.1: triethylamine; tetra-n-butylammonium bromide / palladium(II) acetate / acetonitrile; H₂O

4.1: 98 percent / imidazole; 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 0 °C

5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / Heating

5.2: 81 percent / H₂O₂; NaOH / ethanol / 20 °C

6.1: 90 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 0 - 20 °C

7.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C

7.2: lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / 1 h / -40 °C

7.3: 54 percent / boron trifluoride etherate / diethyl ether; pentane; tetrahydrofuran / 1 h / -40 °C

8.1: 18-crown-6; potassium bistrimethylsilylamide / tetrahydrofuran / 0.33 h / -78 °C

8.2: 94 percent / tetrahydrofuran / 2 h / -78 °C

9.1: 81 percent / lithium perchlorate; 2,6-lutidine / methanol; CH₂Cl₂ / 16.5 h / Electrochemical reaction

10.1: 61 percent / diisobutylaluminum hydride / toluene / 2 h / 20 °C

11.1: 95 percent / NaI; diisopropylamine / tetrahydrofuran / 20 h / Heating

12.1: 100 percent / terta-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; 18-crown-6 ether; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; iodine; tert.-butyl lithium; lithium perchlorate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; B-chlorodiisopinocampheylborane; sodium iodide; palladium diacetate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile; pentane; 3.1: Heck cyclization;
DOI:10.1021/ja0660507

Reference yield:

: (E)-(R)-1-(4-Iodo-furan-3-yl)-4-methyl-hex-4-en-1-ol

: 923275-80-3
9-benzyloxy-8-isopropyl-10-methoxymethoxy-5a,7a-dimethyl-3,4,5,5a,6,7,7a,8,9,10,10a,10b-dodecahydro-2H-1-oxa-benzo[cd]cyclopenta[h]azulen-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: triethylamine; tetra-n-butylammonium bromide / palladium(II) acetate / acetonitrile; H₂O

2.1: 98 percent / imidazole; 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 0 °C

3.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / Heating

3.2: 81 percent / H₂O₂; NaOH / ethanol / 20 °C

4.1: 90 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 0 - 20 °C

5.1: t-BuLi / diethyl ether; pentane / 0.33 h / -78 °C

5.2: lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / 1 h / -40 °C

5.3: 54 percent / boron trifluoride etherate / diethyl ether; pentane; tetrahydrofuran / 1 h / -40 °C

6.1: 18-crown-6; potassium bistrimethylsilylamide / tetrahydrofuran / 0.33 h / -78 °C

6.2: 94 percent / tetrahydrofuran / 2 h / -78 °C

7.1: 81 percent / lithium perchlorate; 2,6-lutidine / methanol; CH₂Cl₂ / 16.5 h / Electrochemical reaction

8.1: 61 percent / diisobutylaluminum hydride / toluene / 2 h / 20 °C

9.1: 95 percent / NaI; diisopropylamine / tetrahydrofuran / 20 h / Heating

10.1: 100 percent / terta-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; 18-crown-6 ether; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; iodine; tert.-butyl lithium; lithium perchlorate; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; sodium iodide; palladium diacetate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; acetonitrile; pentane; 1.1: Heck cyclization;
DOI:10.1021/ja0660507