4-{2-[4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran

Base Information

• Chemical Name: 4-{2-[4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran
• CAS No.: 923275-73-4
• Molecular Formula: C₄₉H₆₈O₄Si₂
• Molecular Weight: 777.248

Synonyms:4-{2-[4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran

Chemical Property of 4-{2-[4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 4-{2-[4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran

There total 11 articles about 4-{2-[4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran 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: 94.0%

2-benzyloxy-4-{2-[7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran-4-yl]-ethyl}-3-isopropyl-4-methyl-cyclopentanone (923275-72-3) + t-butyldimethylsiyl triflate (69739-34-0) → 4-{2-[4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran (923275-73-4)

Guidance literature:

2-benzyloxy-4-{2-[7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran-4-yl]-ethyl}-3-isopropyl-4-methyl-cyclopentanone; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 0.333333h;

t-butyldimethylsiyl triflate; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1021/ja0660507

Reference yield:

(E)-1-(4-Iodo-furan-3-yl)-4-methyl-hex-4-en-1-ol (627075-78-9) → 4-{2-[4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran (923275-73-4)

Guidance literature:

Multi-step reaction with 8 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

With 1H-imidazole; dmap; 18-crown-6 ether; tetrabutylammomium bromide; iodine; tert.-butyl lithium; potassium hexamethylsilazane; Dess-Martin periodane; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; B-chlorodiisopinocampheylborane; palladium diacetate; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; pentane; 3.1: Heck cyclization;

DOI:10.1021/ja0660507

Reference yield:

4-methyl-trans-4-hexenal (27799-31-1) → 4-{2-[4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-isopropyl-1-methyl-cyclopent-2-enyl]-ethyl}-7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran (923275-73-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-BuLi / diethyl ether / -78 °C

1.2: 62 percent / diethyl ether

2.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

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

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

5.1: 98 percent / imidazole; 4-N,N-(dimethylamino)pyridine / CH₂Cl₂ / 0 °C

6.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / Heating

6.2: 81 percent / H₂O₂; NaOH / ethanol / 20 °C

7.1: 90 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 0 - 20 °C

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

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

8.3: 54 percent / boron trifluoride etherate / diethyl ether; pentane; tetrahydrofuran / 1 h / -40 °C

9.1: 18-crown-6; potassium bistrimethylsilylamide / tetrahydrofuran / 0.33 h / -78 °C

9.2: 94 percent / tetrahydrofuran / 2 h / -78 °C

With 1H-imidazole; dmap; n-butyllithium; 18-crown-6 ether; tetrabutylammomium bromide; iodine; tert.-butyl lithium; potassium hexamethylsilazane; Dess-Martin periodane; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; B-chlorodiisopinocampheylborane; palladium diacetate; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; pentane; 4.1: Heck cyclization;

DOI:10.1021/ja0660507

upstream raw materials:

2-benzyloxy-4-{2-[7-(tert-butyl-diphenyl-silanyloxy)-4-methyl-4,5,6,7-tetrahydro-isobenzofuran-4-yl]-ethyl}-3-isopropyl-4-methyl-cyclopentanone

t-butyldimethylsiyl triflate

(4R,7R)-7-Methyl-7-vinyl-4,5,6,7-tetrahydro-isobenzofuran-4-ol

tert-Butyl-((4R,7R)-7-methyl-7-vinyl-4,5,6,7-tetrahydro-isobenzofuran-4-yloxy)-diphenyl-silane

Downstream raw materials:

(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

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

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

9-benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-8-isopropyl-2-methoxy-5a,7a-dimethyl-2,3,4,5,5a,6,7,7a,8,9,10a,10b-dodecahydro-1-oxa-benzo[cd]cyclopenta[h]azulen-10-one

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