5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal

Base Information

Chemical Name:5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal
CAS No.:837383-25-2
Molecular Formula:C₆₀H₁₁₂O₉Si₄
Molecular Weight:1089.89
Hs Code.:

5,11,15-tris-(<i>tert</i>-butyl-dimethyl-silanyloxy)-16-[4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal

Synonyms:5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal

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Chemical Property of 5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal

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Technology Process of 5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal

There total 8 articles about 5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal 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:

: 4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-16-hydroxy-14-(4-methoxy-benzyloxy)-5,7,11,13,15-pentamethyl-hexadeca-3,8-dienyl]-tetrahydro-pyran-2-ol

: 837383-25-2
5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 0 ℃; for 2.5h;
DOI:10.1021/ol0476873

Reference yield:

: tert-Butyl-{(Z)-(1R,2S)-4-iodo-1-[(S)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyloxy}-dimethyl-silane

: 837383-25-2
5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal

Guidance literature:: Multi-step reaction with 7 steps

1.1: ZnCl₂; t-BuLi / diethyl ether; pentane / 1 h / 20 °C

1.2: 60 percent / Pd(PPh₃)4 / diethyl ether; pentane / 20 °C

2.1: 80 percent / H₂O; DDQ / CH₂Cl₂ / 1 h / 0 °C

3.1: 90 percent / PPh₃; imidazole; I₂ / benzene; diethyl ether / 0 - 20 °C

4.1: 82 percent / i-Pr₂NEt / 36 h / 100 °C

5.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -20 - 0 °C

5.2: 31 percent / tetrahydrofuran / 3 h / -20 - -8 °C

6.1: DIBAL-H / CH₂Cl₂ / 0.33 h / 20 °C

7.1: 145 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2.5 h / 0 °C

With 1H-imidazole; water; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; benzene; 7.1: Dess-Martin oxidation;
DOI:10.1021/ol0476873

Reference yield:

: 835929-77-6
(Z)-(2S,3R,4S,8S,9R,10R)-3,9-Bis-(tert-butyl-dimethyl-silanyloxy)-10-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4,8-trimethyl-undec-5-en-1-ol

: 837383-25-2
5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,10,12-pentamethyl-hexadeca-8,13-dienal

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / PPh₃; imidazole; I₂ / benzene; diethyl ether / 0 - 20 °C

2.1: 82 percent / i-Pr₂NEt / 36 h / 100 °C

3.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.75 h / -20 - 0 °C

3.2: 31 percent / tetrahydrofuran / 3 h / -20 - -8 °C

4.1: DIBAL-H / CH₂Cl₂ / 0.33 h / 20 °C

5.1: 145 mg / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2.5 h / 0 °C

With 1H-imidazole; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; benzene; 5.1: Dess-Martin oxidation;
DOI:10.1021/ol0476873