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

Base Information

• Chemical Name: 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
• CAS No.: 926010-59-5
• Molecular Formula: C₆₈H₁₁₈O₉Si₃
• Molecular Weight: 1163.94
• Mol file: 926010-59-5.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 23 articles about 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 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: 62.0%

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)-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 + 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 (926010-59-5)

Guidance literature:

With borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; toluene; at 0 ℃; for 4h; optical yield given as %de; stereoselective reaction;

DOI:10.1002/asia.201000541

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)-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 (926010-59-5)

Guidance literature:

Multi-step reaction with 5 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

5.1: (R)-CBS; BH₃*THF / tetrahydrofuran

With borane-THF; 18-crown-6 ether; [bis(acetoxy)iodo]benzene; boron trichloride - methyl sulfide complex; dicyclohexylboron chloride; potassium carbonate; triethylamine; (R)-(+)-2-methyl-CBS-oxazaborolidine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In tetrahydrofuran; 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)-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 (926010-59-5)

Guidance literature:

Multi-step reaction with 4 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

4.1: (R)-CBS; BH₃*THF / tetrahydrofuran

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

DOI:10.1039/b615122a

upstream raw materials:

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

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

Downstream raw materials:

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