3',4'-bis(tert-butyldimethylsiloxy)-3,5-dihydroxystilbene

Base Information

• Chemical Name: 3',4'-bis(tert-butyldimethylsiloxy)-3,5-dihydroxystilbene
• CAS No.: 1018449-53-0
• Molecular Formula: C₂₆H₄₀O₄Si₂
• Molecular Weight: 472.772
• Mol file: 1018449-53-0.mol

Synonyms:3',4'-bis(tert-butyldimethylsiloxy)-3,5-dihydroxystilbene

Chemical Property of 3',4'-bis(tert-butyldimethylsiloxy)-3,5-dihydroxystilbene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3',4'-bis(tert-butyldimethylsiloxy)-3,5-dihydroxystilbene

There total 14 articles about 3',4'-bis(tert-butyldimethylsiloxy)-3,5-dihydroxystilbene 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: 67.0%

3,4-bis(tert-butyldimethylsilanyloxy)benzaldehyde (99815-16-4) + (3,5-dihydroxybenzyl)triphenylphosphonium bromide (29680-77-1) → 3',4'-bis(tert-butyldimethylsiloxy)-3,5-dihydroxystilbene (1018449-53-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at 18 ℃; for 18h;

DOI:10.1071/CH07044

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3',4'-bis(tert-butyldimethylsiloxy)-3,5-dihydroxystilbene (1018449-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / imidazole / dimethylformamide / 16 h / 18 °C

2: 67 percent / n-BuLi / tetrahydrofuran; hexane / 18 h / 18 °C

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 2: Wittig reaction;

DOI:10.1071/CH07044

Reference yield:

3,4-dihydroxybenzaldehyde (139-85-5) → 3',4'-bis(tert-butyldimethylsiloxy)-3,5-dihydroxystilbene (1018449-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / imidazole / dimethylformamide / 16 h / 18 °C

2: 67 percent / n-BuLi / tetrahydrofuran; hexane / 18 h / 18 °C

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 2: Wittig reaction;

DOI:10.1071/CH07044

upstream raw materials:

C₃₈H₆₈O₄Si₄

3,4-bis(tert-butyldimethylsilanyloxy)benzaldehyde

(3,5-dihydroxybenzyl)triphenylphosphonium bromide

5-(bromomethyl)benzene-1,3-diol

Downstream raw materials:

trans-piceatannol

Refernces

• 1、 Banwell, Martin G,Bezos, Anna,Chand, Satish,Dannhardt, Gerd,Kiefer, Werner,Nowe, Ulrike,Parish, Christopher R,Savage, G Paul,Ulbrich, Holger. "Convergent synthesis and preliminary biological evaluations of the stilbenolignan (+/-)-aiphanol and various congeners.". . p. 2427 - 2429. Retrieved 2007/10/03.