(4-dimethylamino-phenyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-(3,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

Base Information

Chemical Name:(4-dimethylamino-phenyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-(3,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester
CAS No.:835929-66-3
Molecular Formula:C₅₉H₁₀₄N₂O₇Si₃
Molecular Weight:1037.74
Hs Code.:

(4-dimethylamino-phenyl)-carbamic acid 3,9,13-tris-(<i>tert</i>-butyl-dimethyl-silanyloxy)-14-(3,5-dimethyl-6-oxo-3,6-dihydro-2<i>H</i>-pyran-2-yl)-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

Synonyms:(4-dimethylamino-phenyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-(3,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

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Chemical Property of (4-dimethylamino-phenyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-(3,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

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Technology Process of (4-dimethylamino-phenyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-(3,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

There total 11 articles about (4-dimethylamino-phenyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-(3,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester 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: 95.0%

: 835929-40-3
(5R,6S)-3,5-Dimethyl-6-[(3Z,8Z,16Z)-(2S,5S,6S,7S,11S,12R,13R,14S,15S)-2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-hydroxy-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-5,6-dihydro-pyran-2-one

: 16315-59-6
N,N-dimethylaminophenyl isocyanate

: 835929-66-3
(4-dimethylamino-phenyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-(3,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

Guidance literature:: With pyridine; at 20 ℃; for 24h;
DOI:10.1021/ol047686a

Reference yield:

: 835929-53-8
(S)-tert-butyl({1-[(4-methoxybenzyl)oxy]pent-4-en-2-yl}oxy)dimethylsilane

: 835929-66-3
(4-dimethylamino-phenyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-(3,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: O₃ / diethyl ether / 0.33 h / -78 °C

1.2: PPh₃ / CH₂Cl₂ / 1 h / -78 °C

2.1: n-BuLi; t-BuOK / tetrahydrofuran; hexane / 0.33 h / -45 °C

2.2: (+)-β-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / 0.58 h / -78 °C

2.3: 1.21 g / BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

3.1: 80 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / -78 °C

4.1: 75 percent / (4,5-dihydroIMES)(PCy₃)Cl₂Ru=CHPh / CH₂Cl₂ / Heating

5.1: 89 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 °C

6.1: 85 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h / 0 °C

7.1: MeLi-LiBr complex / tetrahydrofuran; pentane / 0.5 h / 0 °C

7.2: 65 percent / tetrahydrofuran; pentane / 4 h / -24 - -10 °C

8.1: 86 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 0 - 20 °C

9.1: 95 percent / pyridine / 24 h / 20 °C

With pyridine; dmap; n-butyllithium; potassium tert-butylate; water; methyllithium; sodium hydrogencarbonate; Dess-Martin periodane; ozone; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; (4,5-dihydroIMES)(PCy₃)Cl₂Ru=CHPh; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; pentane; 7.2: Wittig reaction;
DOI:10.1021/ol047686a

Reference yield:

: 916659-56-8
(S)-3-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)butanal

: 835929-66-3
(4-dimethylamino-phenyl)-carbamic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-(3,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-BuLi; t-BuOK / tetrahydrofuran; hexane / 0.33 h / -45 °C

1.2: (+)-β-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / 0.58 h / -78 °C

1.3: 1.21 g / BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

2.1: 80 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / -78 °C

3.1: 75 percent / (4,5-dihydroIMES)(PCy₃)Cl₂Ru=CHPh / CH₂Cl₂ / Heating

4.1: 89 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 °C

5.1: 85 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h / 0 °C

6.1: MeLi-LiBr complex / tetrahydrofuran; pentane / 0.5 h / 0 °C

6.2: 65 percent / tetrahydrofuran; pentane / 4 h / -24 - -10 °C

7.1: 86 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 0 - 20 °C

8.1: 95 percent / pyridine / 24 h / 20 °C

With pyridine; dmap; n-butyllithium; potassium tert-butylate; water; methyllithium; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; (4,5-dihydroIMES)(PCy₃)Cl₂Ru=CHPh; In tetrahydrofuran; hexane; dichloromethane; pentane; 6.2: Wittig reaction;
DOI:10.1021/ol047686a