(E)-1-(3,5-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxy-phenyl)ethene

Base Information

• Chemical Name: (E)-1-(3,5-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxy-phenyl)ethene
• CAS No.: 192710-95-5
• Molecular Formula: C₄₃H₅₀O₂₁
• Molecular Weight: 902.857
• Mol file: 192710-95-5.mol

Synonyms:(E)-1-(3,5-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxy-phenyl)ethene

Chemical Property of (E)-1-(3,5-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxy-phenyl)ethene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-(3,5-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxy-phenyl)ethene

There total 8 articles about (E)-1-(3,5-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxy-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%

5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol (65728-21-4,33626-08-3) + 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,127061-80-7,142831-80-9) → (E)-1-(3,5-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxy-phenyl)ethene (192710-95-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 0.5h; Inert atmosphere;

DOI:10.1016/j.ejmech.2018.01.037

Reference yield: 32.0%

5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol (65728-21-4,33626-08-3) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (E)-5-hydroxy-4'-methoxy-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)stilbene (197440-96-3) + (E)-1-(3,5-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxy-phenyl)ethene (192710-95-5)

Guidance literature:

With sodium hydroxide; benzyltriethylammonium bromide; In chloroform; water; at 60 ℃; for 10h;

DOI:10.1016/S0008-6215(97)00087-6

Reference yield:

3,5-dihydroxybenzaldehyde (26153-38-8) → (E)-1-(3,5-di-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl)-2-(4'-methoxy-phenyl)ethene (192710-95-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,N-diisopropylethylamine / dimethylformamide / 0.5 h / 20 °C

2.1: butyllithium / hexane; tetrahydrofuran / 15 - 20 °C

2.2: 78 percent / hexane; tetrahydrofuran / 1 h / 20 °C

3.1: 68.3 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C

4.1: 13 percent / benzyltriethylammonium bromide; NaOH / CHCl₃; H₂O / 10 h / 60 °C

With sodium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; benzyltriethylammonium bromide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; chloroform; water; N,N-dimethyl-formamide; 1.1: silylation / 2.1: deprotonation / 2.2: Wittig reaction / 3.1: desilylation / 4.1: glucosylation;

DOI:10.1016/S0008-6215(97)00087-6

upstream raw materials:

5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

3,5-dihydroxybenzaldehyde

(4-methoxybenzyl)triphenylphosphonium bromide