(3Z,5S,6S,7S,8R,11R,13S,14R,15S,16Z,18S,20S,21R,22E)-6-(4-methoxybenzyloxy)-14,18,20-tris(tert-butyldimethylsilyloxy)-5,7,11,13,15,21-hexamethyl-24-(trityloxy)tetracosa-1,3,16,22-tetraen-8-ol

Base Information

• Chemical Name: (3Z,5S,6S,7S,8R,11R,13S,14R,15S,16Z,18S,20S,21R,22E)-6-(4-methoxybenzyloxy)-14,18,20-tris(tert-butyldimethylsilyloxy)-5,7,11,13,15,21-hexamethyl-24-(trityloxy)tetracosa-1,3,16,22-tetraen-8-ol
• CAS No.: 945402-27-7
• Molecular Formula: C₇₅H₁₁₈O₇Si₃
• Molecular Weight: 1216.01
• Mol file: 945402-27-7.mol

Synonyms:(3Z,5S,6S,7S,8R,11R,13S,14R,15S,16Z,18S,20S,21R,22E)-6-(4-methoxybenzyloxy)-14,18,20-tris(tert-butyldimethylsilyloxy)-5,7,11,13,15,21-hexamethyl-24-(trityloxy)tetracosa-1,3,16,22-tetraen-8-ol

Chemical Property of (3Z,5S,6S,7S,8R,11R,13S,14R,15S,16Z,18S,20S,21R,22E)-6-(4-methoxybenzyloxy)-14,18,20-tris(tert-butyldimethylsilyloxy)-5,7,11,13,15,21-hexamethyl-24-(trityloxy)tetracosa-1,3,16,22-tetraen-8-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3Z,5S,6S,7S,8R,11R,13S,14R,15S,16Z,18S,20S,21R,22E)-6-(4-methoxybenzyloxy)-14,18,20-tris(tert-butyldimethylsilyloxy)-5,7,11,13,15,21-hexamethyl-24-(trityloxy)tetracosa-1,3,16,22-tetraen-8-ol

There total 1 articles about (3Z,5S,6S,7S,8R,11R,13S,14R,15S,16Z,18S,20S,21R,22E)-6-(4-methoxybenzyloxy)-14,18,20-tris(tert-butyldimethylsilyloxy)-5,7,11,13,15,21-hexamethyl-24-(trityloxy)tetracosa-1,3,16,22-tetraen-8-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: 91.0%

(3Z,5S,6S,7R,11R,13S,14R,15S,16Z,18S,20S,21R,22E)-6-(4-methoxybenzyloxy)-14,18,20-tris(tert-butyldimethylsilyloxy)-5,7,11,13,15,21-hexamethyl-24-(trityloxy)tetracosa-1,3,16,22-tetraen-8-one → (3Z,5S,6S,7S,8R,11R,13S,14R,15S,16Z,18S,20S,21R,22E)-6-(4-methoxybenzyloxy)-14,18,20-tris(tert-butyldimethylsilyloxy)-5,7,11,13,15,21-hexamethyl-24-(trityloxy)tetracosa-1,3,16,22-tetraen-8-ol (945402-27-7)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jm061385k

Reference yield:

(3Z,5S,6S,7S,8R,11R,13S,14R,15S,16Z,18S,20S,21R,22E)-6-(4-methoxybenzyloxy)-14,18,20-tris(tert-butyldimethylsilyloxy)-5,7,11,13,15,21-hexamethyl-24-(trityloxy)tetracosa-1,3,16,22-tetraen-8-ol (945402-27-7) → (2E,4R,5S,7S,8Z,10S,11R,12S,14R,17R,18R,19S,20S,21Z)-19-(4-methoxybenzyloxy)-5,7,11,17-tetrakis(tert-butyldimethylsilyloxy)-4,10,12,14,18,20-hexamethyltetracosa-2,8,21,23-tetraen-1-ol (945401-98-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h

2: 85 percent / ZnBr₂ / CH₂Cl₂; methanol / 20 h / 0 °C

With 2,6-dimethylpyridine; zinc dibromide; In methanol; dichloromethane;

DOI:10.1021/jm061385k

Reference yield:

(3Z,5S,6S,7S,8R,11R,13S,14R,15S,16Z,18S,20S,21R,22E)-6-(4-methoxybenzyloxy)-14,18,20-tris(tert-butyldimethylsilyloxy)-5,7,11,13,15,21-hexamethyl-24-(trityloxy)tetracosa-1,3,16,22-tetraen-8-ol (945402-27-7) → (2Z,4E,6R,7S,9S,10Z,12S,13R,14S,16R,19R,20R,21S,22S,23Z)-methyl 21-(4-methoxybenzyloxy)-7,9,13-tris(tert-butyldimethylsilyloxy)-19-(tert-butyldimethylsilyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate (960076-51-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h

2: 85 percent / ZnBr₂ / CH₂Cl₂; methanol / 20 h / 0 °C

3: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

4: 0.274 g / 18-crown-6; potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 3.17 h / -78 °C

With 2,6-dimethylpyridine; 18-crown-6 ether; potassium hexamethylsilazane; Dess-Martin periodane; zinc dibromide; In tetrahydrofuran; methanol; dichloromethane; toluene; 3: Dess-Martin oxidation / 4: Still-Gennari olefination;

DOI:10.1021/jm061385k

Downstream raw materials:

(2E,4R,5S,7S,8Z,10S,11R,12S,14R,17R,18R,19S,20S,21Z)-19-(4-methoxybenzyloxy)-5,7,11,17-tetrakis(tert-butyldimethylsilyloxy)-4,10,12,14,18,20-hexamethyltetracosa-2,8,21,23-tetraen-1-ol

(2Z,4E,6R,7S,9S,10Z,12S,13R,14S,16R,19R,20R,21S,22S,23Z)-methyl 21-(4-methoxybenzyloxy)-7,9,13-tris(tert-butyldimethylsilyloxy)-19-(tert-butyldimethylsilyloxy)-6,12,14,16,20,22-hexamethylhexacosa-2,4,10,23,25-pentaenoate