5,13,19-tris-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1,21-bis-(4-methoxy-benzyloxy)-4,6,12,14,16,18,20,22-octamethyl-hexacosa-2,10,15,23,25-pentaen-9-one

Base Information

• Chemical Name: 5,13,19-tris-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1,21-bis-(4-methoxy-benzyloxy)-4,6,12,14,16,18,20,22-octamethyl-hexacosa-2,10,15,23,25-pentaen-9-one
• CAS No.: 926010-58-4
• Molecular Formula: C₆₈H₁₁₆O₉Si₃
• Molecular Weight: 1161.92
• Mol file: 926010-58-4.mol

Synonyms:5,13,19-tris-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1,21-bis-(4-methoxy-benzyloxy)-4,6,12,14,16,18,20,22-octamethyl-hexacosa-2,10,15,23,25-pentaen-9-one

Chemical Property of 5,13,19-tris-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1,21-bis-(4-methoxy-benzyloxy)-4,6,12,14,16,18,20,22-octamethyl-hexacosa-2,10,15,23,25-pentaen-9-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,13,19-tris-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1,21-bis-(4-methoxy-benzyloxy)-4,6,12,14,16,18,20,22-octamethyl-hexacosa-2,10,15,23,25-pentaen-9-one

There total 20 articles about 5,13,19-tris-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1,21-bis-(4-methoxy-benzyloxy)-4,6,12,14,16,18,20,22-octamethyl-hexacosa-2,10,15,23,25-pentaen-9-one 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: 48.0%

3-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-5-enal + 6,12-bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraen-2-one → 5,13,19-tris-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1,21-bis-(4-methoxy-benzyloxy)-4,6,12,14,16,18,20,22-octamethyl-hexacosa-2,10,15,23,25-pentaen-9-one (926010-58-4) + 5,13,19-tris-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1,21-bis-(4-methoxy-benzyloxy)-4,6,12,14,16,18,20,22-octamethyl-hexacosa-2,10,15,23,25-pentaen-9-one

Guidance literature:

3-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-5-enal; 6,12-bis-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraen-2-one; With dicyclohexylboron chloride; triethylamine; In diethyl ether; at 0 ℃;

In diethyl ether; at -78 ℃; pH=7;

DOI:10.1039/b615122a

Reference yield:

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) → 5,13,19-tris-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1,21-bis-(4-methoxy-benzyloxy)-4,6,12,14,16,18,20,22-octamethyl-hexacosa-2,10,15,23,25-pentaen-9-one (926010-58-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / BCl₃*DMS / CH₂Cl₂

2.1: 99 percent / PhI(OAc)2 / TEMPO / CH₂Cl₂

3.1: 85 percent / 18-C-6; K₂CO₃ / toluene; hexamethylphosphoric acid triamide

4.1: Et₃N; c-Hex₂BCl / diethyl ether / 0 °C

4.2: 48 percent / diethyl ether / -78 °C / pH 7

With 18-crown-6 ether; [bis(acetoxy)iodo]benzene; boron trichloride - methyl sulfide complex; dicyclohexylboron chloride; potassium carbonate; triethylamine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; toluene; 3.1: Still-Gennari olefination;

DOI:10.1039/b615122a

Reference yield:

(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-trien-1-ol (252342-46-4) → 5,13,19-tris-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-1,21-bis-(4-methoxy-benzyloxy)-4,6,12,14,16,18,20,22-octamethyl-hexacosa-2,10,15,23,25-pentaen-9-one (926010-58-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 99 percent / PhI(OAc)2 / TEMPO / CH₂Cl₂

2.1: 85 percent / 18-C-6; K₂CO₃ / toluene; hexamethylphosphoric acid triamide

3.1: Et₃N; c-Hex₂BCl / diethyl ether / 0 °C

3.2: 48 percent / diethyl ether / -78 °C / pH 7

With 18-crown-6 ether; [bis(acetoxy)iodo]benzene; dicyclohexylboron chloride; potassium carbonate; triethylamine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; toluene; 2.1: Still-Gennari olefination;

DOI:10.1039/b615122a

upstream raw materials:

3,9-bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-trienal

(2S,3R,4S)-5-[(4-methoxybenzyl)oxy]-2,4-dimethylpentane-1,3-diol

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

(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-5,13,15-trien-1-ol

Downstream raw materials:

5,13,19-tris-(tert-butyl-dimethyl-silanyloxy)-1,21-bis-(4-methoxy-benzyloxy)-4,6,12,14,16,18,20,22-octamethyl-hexacosa-2,10,15,23,25-pentaene-7,9-diol

4-[4,10-bis-(tert-butyl-dimethyl-silanyloxy)-12-(4-methoxy-benzyloxy)-3,5,7,9,11,13-hexamethyl-heptadeca-1,6,14,16-tetraenyl]-6-[2-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-1,3-dimethyl-hex-4-enyl]-2,2-dimethyl-[1,3]dioxane