(3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-fluoro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol

Base Information

• Chemical Name: (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-fluoro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol
• CAS No.: 706815-56-7
• Molecular Formula: C₄₃H₇₅FO₃Si₂
• Molecular Weight: 715.236

Synonyms:

Chemical Property of (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-fluoro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-fluoro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol

There total 9 articles about (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-fluoro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-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:

bromo(3-fluorophenyl)magnesium (17318-03-5) → (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-fluoro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol (706815-56-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 9-BBN

1.2: aq. H₂O₂; NaOH

2.1: I₂; PPh₃; imidazole

3.1: toluene / 80 °C

4.1: n-BuLi

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; iodine; triphenylphosphine; In toluene; 5.1: Wittig reaction;

DOI:10.1016/j.bmcl.2004.01.102

Reference yield:

3-(3-fluorophenyl)propan-1-ol (156868-83-6) → (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-fluoro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol (706815-56-7)

Guidance literature:

Multi-step reaction with 3 steps

1: I₂; PPh₃; imidazole

2: toluene / 80 °C

3: n-BuLi

With 1H-imidazole; n-butyllithium; iodine; triphenylphosphine; In toluene; 3: Wittig reaction;

DOI:10.1016/j.bmcl.2004.01.102

Reference yield:

1-fluoro-3-(3-iodo-propyl)-benzene → (3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-fluoro-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol (706815-56-7)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene / 80 °C

2: n-BuLi

With n-butyllithium; In toluene; 2: Wittig reaction;

DOI:10.1016/j.bmcl.2004.01.102

upstream raw materials:

(5Z,13Z)-(2R,3R,4S,8S,9R,10R,11S,12S)-3,9-bis(tertbutyldimethylsilanyloxy)-11-hydroxy-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienal

1-allyl-3-fluorobenzene

bromo(3-fluorophenyl)magnesium

3-(3-fluorophenyl)propan-1-ol

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