1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene

Base Information

• Chemical Name: 1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene
• CAS No.: 256920-81-7
• Molecular Formula: C₅₀H₈₄O₆Si₂
• Molecular Weight: 837.384
• Mol file: 256920-81-7.mol

Synonyms:1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene

Chemical Property of 1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene

There total 58 articles about 1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-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: 99.0%

t-butyldimethylsiyl triflate (69739-34-0) + (3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-hexadeca-1,3,11-trien-8-ol (261968-22-3) → 1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene (256920-81-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ja011211m

Reference yield: 82.0%

t-butyldimethylsiyl triflate (69739-34-0) + (2S,3R,4S,5Z,8S,9R,10S,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-triene-3,9-diol (373645-72-8) → 1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene (256920-81-7)

Guidance literature:

With triethylamine; In dichloromethane; at -78 - 0 ℃; for 5h;

DOI:10.1021/ja011211m

Reference yield: 81.0%

(1-bromoallyl)trimethylsilane (94397-40-7) + (Z)-(2R,3R,4R,5R,6S,10S,11R,12S)-5,11-bis(tert-butyldimethylsilanyloxy)-3,13-bis(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-enal (256920-80-6) → 1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene (256920-81-7)

Guidance literature:

(1-bromoallyl)trimethylsilane; (Z)-(2R,3R,4R,5R,6S,10S,11R,12S)-5,11-bis(tert-butyldimethylsilanyloxy)-3,13-bis(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-enal; With chromium dichloride; In tetrahydrofuran; at 0 - 15 ℃; for 1.25h; Large scale;

With potassium hydroxide; In tetrahydrofuran; methanol; at 0 - 25 ℃; for 16h; Large scale;

DOI:10.1021/op034133r

upstream raw materials:

t-butyldimethylsiyl triflate

(3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-hexadeca-1,3,11-trien-8-ol

(Z)-(2R,3R,4R,5R,6S,10S,11R,12S)-5,11-bis(tert-butyldimethylsilanyloxy)-3,13-bis(4-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyltridec-8-enal

(2S,3R,4S,5Z,8S,9R,10S,11S,12S,13Z)-1,11-bis-(p-methoxybenzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-triene-3,9-diol

Downstream raw materials:

C₄₅H₇₈O₅Si₂

(3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-5,7,9,11,13,15-hexamethyl-19-(4-phenoxy-phenyl)-nonadeca-1,3,11,16-tetraen-6-ol

(3Z,11Z,16Z)-(5S,6S,7R,8R,9S,13S,14S,15S)-8,14-Bis-(tert-butyl-dimethyl-silanyloxy)-19-(3-fluoro-4-methyl-phenyl)-5,7,9,11,13,15-hexamethyl-nonadeca-1,3,11,16-tetraen-6-ol

3-[(3Z,8Z,16Z)-(5S,6S,7S,11S,12R,13R,14S,15S)-6,12-Bis-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-2-methyl-phenol