1-[3R,9R-bis-(tert-butyldimethylsilanyloxy)-12-iodo-2R,8S,10S-trimethyl-1S-(1S-methylpent-2Z-enyl)-dodec-11Z-enyloxymethyl]-4-methoxybenzene

Base Information

• Chemical Name: 1-[3R,9R-bis-(tert-butyldimethylsilanyloxy)-12-iodo-2R,8S,10S-trimethyl-1S-(1S-methylpent-2Z-enyl)-dodec-11Z-enyloxymethyl]-4-methoxybenzene
• CAS No.: 1234500-98-1
• Molecular Formula: C₄₁H₇₅IO₄Si₂
• Molecular Weight: 815.12

Synonyms:1-[3R,9R-bis-(tert-butyldimethylsilanyloxy)-12-iodo-2R,8S,10S-trimethyl-1S-(1S-methylpent-2Z-enyl)-dodec-11Z-enyloxymethyl]-4-methoxybenzene

Chemical Property of 1-[3R,9R-bis-(tert-butyldimethylsilanyloxy)-12-iodo-2R,8S,10S-trimethyl-1S-(1S-methylpent-2Z-enyl)-dodec-11Z-enyloxymethyl]-4-methoxybenzene

Chemical Property:

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Technology Process of 1-[3R,9R-bis-(tert-butyldimethylsilanyloxy)-12-iodo-2R,8S,10S-trimethyl-1S-(1S-methylpent-2Z-enyl)-dodec-11Z-enyloxymethyl]-4-methoxybenzene

There total 2 articles about 1-[3R,9R-bis-(tert-butyldimethylsilanyloxy)-12-iodo-2R,8S,10S-trimethyl-1S-(1S-methylpent-2Z-enyl)-dodec-11Z-enyloxymethyl]-4-methoxybenzene 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: 92.0%

14R-(tert-butyldimethylsilanyloxy)-17-iodo-6S-(4-methoxybenzyloxy)-5S,7S,13S,15S-tetramethylheptadeca-3Z,16Z-dien-8R-ol (1234501-23-5) + t-butyldimethylsiyl triflate (69739-34-0) → 1-[3R,9R-bis-(tert-butyldimethylsilanyloxy)-12-iodo-2R,8S,10S-trimethyl-1S-(1S-methylpent-2Z-enyl)-dodec-11Z-enyloxymethyl]-4-methoxybenzene (1234500-98-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ja103537u

Reference yield: 66.0%

3R,9R-bis-(tert-butyldimethylsilanyloxy)-11S-(4-methoxybenzyloxy)-2R,4S,10R,12S-tetramethylhexadec-13Z-enal (1234501-17-7) + (iodomethyl)triphenylphosphonium iodide (3020-28-8) → 1-[3R,9R-bis-(tert-butyldimethylsilanyloxy)-12-iodo-2R,8S,10S-trimethyl-1S-(1S-methylpent-2Z-enyl)-dodec-11Z-enyloxymethyl]-4-methoxybenzene (1234500-98-1)

Guidance literature:

(iodomethyl)triphenylphosphonium iodide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 0.333333h; Inert atmosphere;

3R,9R-bis-(tert-butyldimethylsilanyloxy)-11S-(4-methoxybenzyloxy)-2R,4S,10R,12S-tetramethylhexadec-13Z-enal; In tetrahydrofuran; at -78 - 20 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ja103537u

Reference yield: 24.0%

methyl (2Z,4E)-(6R,7S)-7-(tert-butyldimethylsilyloxy)-6-methyl-9-oxo-nona-2,4-dienoate (945402-29-9) + 1-[3R,9R-bis-(tert-butyldimethylsilanyloxy)-12-iodo-2R,8S,10S-trimethyl-1S-(1S-methylpent-2Z-enyl)-dodec-11Z-enyloxymethyl]-4-methoxybenzene (1234500-98-1) → 1S-[3R,9R-bis-(tert-butyldimethylsilanyloxy)-2R,8S,10S-trimethyl-1-(1S-methylpent-2Z-enyl)-dodec-11-enyloxymethyl]-4-methoxybenzene (1234501-25-7) + methyl 7S,13R,19R-tris(tert-butyldimethylsilanyloxy)-9R-hydroxy-21S-(4-methoxy-benzyloxy)-6R,12S,14S,20R,22S-pentamethylhexacosa-2Z,4E,10Z,23Z-tetraenoate (1234501-77-9) + methyl 7S,13R,19R-tris(tert-butyldimethylsilanyloxy)-9S-hydroxy-21S-(4-methoxy-benzyloxy)-6R,12S,14S,20R,22S-pentamethylhexacosa-2Z,4E,10Z,23Z-tetraenoate (1234501-76-8)

Guidance literature:

1-[3R,9R-bis-(tert-butyldimethylsilanyloxy)-12-iodo-2R,8S,10S-trimethyl-1S-(1S-methylpent-2Z-enyl)-dodec-11Z-enyloxymethyl]-4-methoxybenzene; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 1h; Inert atmosphere;

methyl (2Z,4E)-(6R,7S)-7-(tert-butyldimethylsilyloxy)-6-methyl-9-oxo-nona-2,4-dienoate; In diethyl ether; pentane; at -78 ℃; Inert atmosphere;

With ammonium chloride; In diethyl ether; pentane; Inert atmosphere;

DOI:10.1021/ja103537u

upstream raw materials:

3R,9R-bis-(tert-butyldimethylsilanyloxy)-11S-(4-methoxybenzyloxy)-2R,4S,10R,12S-tetramethylhexadec-13Z-enal

(iodomethyl)triphenylphosphonium iodide

14R-(tert-butyldimethylsilanyloxy)-17-iodo-6S-(4-methoxybenzyloxy)-5S,7S,13S,15S-tetramethylheptadeca-3Z,16Z-dien-8R-ol

t-butyldimethylsiyl triflate

Downstream raw materials:

1S-[3R,9R-bis-(tert-butyldimethylsilanyloxy)-2R,8S,10S-trimethyl-1-(1S-methylpent-2Z-enyl)-dodec-11-enyloxymethyl]-4-methoxybenzene

methyl 7S,13R,19R-tris(tert-butyldimethylsilanyloxy)-9R-hydroxy-21S-(4-methoxy-benzyloxy)-6R,12S,14S,20R,22S-pentamethylhexacosa-2Z,4E,10Z,23Z-tetraenoate

methyl 7S,13R,19R-tris(tert-butyldimethylsilanyloxy)-9S-hydroxy-21S-(4-methoxy-benzyloxy)-6R,12S,14S,20R,22S-pentamethylhexacosa-2Z,4E,10Z,23Z-tetraenoate

methyl 7S,13R,19R-tris(tert-butyldimethylsilanyloxy)-9R-hydroxy-21S-(4-methoxy-benzyloxy)-6S,12S,14S,20R,22S-pentamethylhexacosa-2Z,4E,10Z,23Z-tetraenoate

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