2H-Pyran-2-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(1E,3R,4R,6R,7Z,9Z,11E)-6-[ [(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[[(1,1-dimethylethyl)diphenylsilyl] oxy]-4-hydroxy-3-methyl-3-[(triethylsilyl)oxy]-1,7,9,11-tridecatetraen-1-yl] -5,6-dihydro-, (5S,6S)-

Base Information

• Chemical Name: 2H-Pyran-2-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(1E,3R,4R,6R,7Z,9Z,11E)-6-[ [(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[[(1,1-dimethylethyl)diphenylsilyl] oxy]-4-hydroxy-3-methyl-3-[(triethylsilyl)oxy]-1,7,9,11-tridecatetraen-1-yl] -5,6-dihydro-, (5S,6S)-
• CAS No.: 915700-53-7
• Molecular Formula: C53H86O7Si4
• Molecular Weight: 947.604
• Mol file: 915700-53-7.mol

Synonyms:

Chemical Property of 2H-Pyran-2-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(1E,3R,4R,6R,7Z,9Z,11E)-6-[ [(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[[(1,1-dimethylethyl)diphenylsilyl] oxy]-4-hydroxy-3-methyl-3-[(triethylsilyl)oxy]-1,7,9,11-tridecatetraen-1-yl] -5,6-dihydro-, (5S,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Pyran-2-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(1E,3R,4R,6R,7Z,9Z,11E)-6-[ [(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[[(1,1-dimethylethyl)diphenylsilyl] oxy]-4-hydroxy-3-methyl-3-[(triethylsilyl)oxy]-1,7,9,11-tridecatetraen-1-yl] -5,6-dihydro-, (5S,6S)-

There total 1 articles about 2H-Pyran-2-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[(1E,3R,4R,6R,7Z,9Z,11E)-6-[ [(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[[(1,1-dimethylethyl)diphenylsilyl] oxy]-4-hydroxy-3-methyl-3-[(triethylsilyl)oxy]-1,7,9,11-tridecatetraen-1-yl] -5,6-dihydro-, (5S,6S)- 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:

(5S,6S,1'E,3'R,4'R,6'R,7'EZ)-5-(tert-butyl(dimethyl)silyloxy)-6-[6'-(tert-butyl(dimethyl)silyloxy)-8'-iodo-3'-methyl-3',4'-bis(triethylsilyloxy)-1',7'-octadienyl]-5,6-dihydro-2H-pyran-2-one → (5S,6S,1'E,3'R,4'R,6'R,7'Z,9'Z,11'Z)-5-(tert-butyl(dimethyl)silyloxy)-6-[6'-(tert-butyl(dimethyl)silyloxy)-13-(tert-butyl(diphenyl)silyloxy)-4'-hydroxy-3'-methyl-3'-(triethylsilyloxy)-1',7',9',11'-tridecatetraenyl]-5,6-dihydro-2H-pyran-2-one (915700-53-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 37 percent / HCl / tetrahydrofuran; acetonitrile / 4 h / -10 °C

2: 96 percent / Pd(MeCN)2Cl₂ / dimethylformamide / 12 h / 0 °C

With hydrogenchloride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; 2: Stille coupling;

DOI:10.1021/ol062111u

Reference yield:

(5S,6S,1'E,3'R,4'R,6'R,7'Z,9'Z,11'Z)-5-(tert-butyl(dimethyl)silyloxy)-6-[6'-(tert-butyl(dimethyl)silyloxy)-13-(tert-butyl(diphenyl)silyloxy)-4'-hydroxy-3'-methyl-3'-(triethylsilyloxy)-1',7',9',11'-tridecatetraenyl]-5,6-dihydro-2H-pyran-2-one (915700-53-7) + diallyl diisopropylphosphoramidite (126429-21-8) → phosphorous acid diallyl ester 3-(tert-butyl-dimethyl-silanyloxy)-1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-methyl-1-triethylsilanyloxy-allyl}-10-(tert-butyl-diphenyl-silanyloxy)-deca-4,6,8-trienyl ester

Guidance literature:

With 1H-tetrazole; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1021/ol062111u

Reference yield:

(5S,6S,1'E,3'R,4'R,6'R,7'Z,9'Z,11'Z)-5-(tert-butyl(dimethyl)silyloxy)-6-[6'-(tert-butyl(dimethyl)silyloxy)-13-(tert-butyl(diphenyl)silyloxy)-4'-hydroxy-3'-methyl-3'-(triethylsilyloxy)-1',7',9',11'-tridecatetraenyl]-5,6-dihydro-2H-pyran-2-one (915700-53-7) → phosphoric acid mono-[3-(tert-butyl-dimethyl-silanyloxy)-1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-methyl-1-triethylsilanyloxy-allyl}-10-(tert-butyl-diphenyl-silanyloxy)-deca-4,6,8-trienyl] ester (1054709-06-6)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrazole / CH₂Cl₂ / 0.25 h / 20 °C

2: 99 mg / TBHP / CH₂Cl₂; methanol / 3.5 h / 0 °C

3: Et₃N; formic acid; Pd(PPh₃)4 / tetrahydrofuran / 1 h / 50 °C

With 1H-tetrazole; tert.-butylhydroperoxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol062111u

Downstream raw materials:

phosphoric acid mono-[3-(tert-butyl-dimethyl-silanyloxy)-1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-methyl-1-triethylsilanyloxy-allyl}-10-(tert-butyl-diphenyl-silanyloxy)-deca-4,6,8-trienyl] ester

phosphoric acid diallyl ester 3-(tert-butyl-dimethyl-silanyloxy)-1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-methyl-1-triethylsilanyloxy-allyl}-10-(tert-butyl-diphenyl-silanyloxy)-deca-4,6,8-trienyl ester