Benzaldehyde, 3,4,5-trimethoxy-, O-[(2E,4E)-8-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-methyl-8-(2-thienyl) -2,4-octadienyl]oxime

Base Information

Chemical Name:Benzaldehyde, 3,4,5-trimethoxy-, O-[(2E,4E)-8-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-methyl-8-(2-thienyl) -2,4-octadienyl]oxime
CAS No.:392336-41-3
Molecular Formula:C39H47NO5SSi
Molecular Weight:669.957
Hs Code.:
Mol file:392336-41-3.mol

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Chemical Property of Benzaldehyde, 3,4,5-trimethoxy-, O-[(2E,4E)-8-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-methyl-8-(2-thienyl) -2,4-octadienyl]oxime

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Technology Process of Benzaldehyde, 3,4,5-trimethoxy-, O-[(2E,4E)-8-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-methyl-8-(2-thienyl) -2,4-octadienyl]oxime

There total 5 articles about Benzaldehyde, 3,4,5-trimethoxy-, O-[(2E,4E)-8-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-methyl-8-(2-thienyl) -2,4-octadienyl]oxime 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: 51.0%

: 65567-36-4
(E)-3,4,5-Trimethoxybenzaldehydoxim

: 392336-40-2
tert-butyl-(1RS,2E,4E)-(8-chloro-4-methyl-1-thiophen-2-ylocta-4,6-dienyloxy)diphenylsilane

: 392336-41-3
3,4,5-trimethoxybenzaldehyde O-[(2E,4E,8RS)-8-(tert-butyldiphenylsilanyloxy)-5-methyl-8-thiophen-2-ylocta-2,4-dienyl]oxime

Guidance literature:: (E)-3,4,5-Trimethoxybenzaldehydoxim; With sodium hydride; In tetrahydrofuran; for 1h;

tert-butyl-(1RS,2E,4E)-(8-chloro-4-methyl-1-thiophen-2-ylocta-4,6-dienyloxy)diphenylsilane; In tetrahydrofuran; for 16h; Further stages.;
DOI:10.1021/jm0105171

Reference yield:

: 392336-35-5
(2E,6RS)-3-methyl-6-thiophen-2-ylhex-2-ene-1,6-diol

: 392336-41-3
3,4,5-trimethoxybenzaldehyde O-[(2E,4E,8RS)-8-(tert-butyldiphenylsilanyloxy)-5-methyl-8-thiophen-2-ylocta-2,4-dienyl]oxime

Guidance literature:: Multi-step reaction with 8 steps

1.1: 58 percent / imidazole / CH₂Cl₂ / 2 h / 0 °C

2.1: 71 percent / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h

3.1: 99 percent / pyridinium p-toluenesulfonate / ethanol / 18 h / 20 °C

4.1: 92 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h

5.1: 47 percent / CH₂Cl₂ / 14 h / 40 °C

6.1: 83 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

7.1: LiCl; s-collidine; methanesulfonyl chloride / dimethylformamide / 2 h / 0 - 20 °C

8.1: NaH / tetrahydrofuran / 1 h

8.2: 51 percent / tetrahydrofuran / 16 h

With 1H-imidazole; 2,4,6-trimethyl-pyridine; dmap; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; pyridinium chlorochromate; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 5.1: Wittig homologation;
DOI:10.1021/jm0105171

Reference yield:

: 392336-39-9
(2E,4E,8RS)-8-(tert-butyldimethylsilanyloxy)-5-methyl-8-thiophen-2-ylocta-2,4-dien-1-ol

: 392336-41-3
3,4,5-trimethoxybenzaldehyde O-[(2E,4E,8RS)-8-(tert-butyldiphenylsilanyloxy)-5-methyl-8-thiophen-2-ylocta-2,4-dienyl]oxime

Guidance literature:: Multi-step reaction with 2 steps

1.1: LiCl; s-collidine; methanesulfonyl chloride / dimethylformamide / 2 h / 0 - 20 °C

2.1: NaH / tetrahydrofuran / 1 h

2.2: 51 percent / tetrahydrofuran / 16 h

With 2,4,6-trimethyl-pyridine; sodium hydride; methanesulfonyl chloride; lithium chloride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jm0105171