(E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene

Base Information

• Chemical Name: (E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene
• CAS No.: 892402-78-7
• Molecular Formula: C₆₀H₆₆O₁₂Si₂
• Molecular Weight: 1035.35
• Mol file: 892402-78-7.mol

Synonyms:(E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene

Chemical Property of (E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene

There total 4 articles about (E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene 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: 80.0%

(E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-(4-hydroxyphenyl)ethene (827348-00-5) + 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate (339276-12-9) → (E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene (892402-78-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at 0 - 25 ℃; for 5h;

DOI:10.1055/s-2006-926394

Reference yield: 60.0%

(E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-(4-hydroxyphenyl)ethene (827348-00-5) + 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate (151767-11-2) → (E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene (892402-78-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; Molecular sieve;

DOI:10.1021/jm1007006

Reference yield:

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0) → (E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-[4-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyloxy)phenyl]ethene (892402-78-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 10 percent / imidazole / dimethylformamide / 6 h / -5 - 20 °C

2: 80 percent / 4 Angstroem molecular sieves; trimethylsilyl triflate / CH₂Cl₂ / 5 h / 0 - 25 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2006-926394

upstream raw materials:

(E)-1-(3,5-bis-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-2-(4-hydroxyphenyl)ethene

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol

tert-butyldimethylsilyl chloride

Downstream raw materials:

trans-resveratroloside