3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde

Base Information

• Chemical Name: 3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde
• CAS No.: 203179-62-8
• Molecular Formula: C₂₅H₃₀O₁₃
• Molecular Weight: 538.505
• Mol file: 203179-62-8.mol

Synonyms:3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde

Chemical Property of 3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde

There total 9 articles about 3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde 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:

(E)-sinapinaldehyde (4206-58-0,20649-43-8) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde (203179-62-8)

Guidance literature:

With potassium hydroxide; diethyl ether;

Reference yield:

syringic aldehyde (134-96-3) → 3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde (203179-62-8)

Guidance literature:

Multi-step reaction with 3 steps

1: TDA-1, aq. K₂CO₃ / CH₂Cl₂ / 15 h / 40 °C

2: TDA-1, aq. K₂CO₃ / CH₂Cl₂ / 24 h / Heating

3: 1.) Br₂, 2.) aq. AcOH / 1.) CCl₄, 20 deg C, 1 h, 2.) r.t., 10 h

With bromine; potassium carbonate; acetic acid; In dichloromethane;

DOI:10.1055/s-1998-2009

Reference yield:

4-acetoxy-3,5-dimethoxybenzaldehyde (53669-33-3) → 3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde (203179-62-8)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate; Tris(3,6-dioxaheptyl)amine / dichloromethane / 12 h / 20 °C

2: hydrogenchloride / water; dichloromethane / 12 h / 20 °C

3: potassium carbonate; water / tetrahydrofuran / 1 h / 65 °C

4: tetrabutylammomium bromide / chloroform; water; tetrahydrofuran / 2 h / 65 °C

With hydrogenchloride; Tris(3,6-dioxaheptyl)amine; tetrabutylammomium bromide; water; potassium carbonate; In tetrahydrofuran; dichloromethane; chloroform; water;

DOI:10.1021/acs.jnatprod.1c00585

upstream raw materials:

(E)-sinapinaldehyde

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

D-glucose pentaacetate

3,5-dimethoxy-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzaldehyde

Downstream raw materials:

Syringenin

sinapyl aldehyde 4-O-β-D-glucopyranoside

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

syringin

Refernces

• 1、 Daubresse, Nicolas,Francesch, Charlette,Mhamdi, Farida,Rolando, Christian. "Coniferin and derivatives: A fast and easy synthesis via the aldehyde series using phase-transfer catalysis". . p. 157 - 161. Retrieved 2007/10/03.