methyl 4-O-β-glucopyranosyl-(E)-caffeate

Base Information

• Chemical Name: methyl 4-O-β-glucopyranosyl-(E)-caffeate
• CAS No.: 499-21-8
• Molecular Formula: C₁₆H₂₀O₉
• Molecular Weight: 356.329
• Mol file: 499-21-8.mol

Synonyms:methyl 4-O-β-glucopyranosyl-(E)-caffeate

Chemical Property of methyl 4-O-β-glucopyranosyl-(E)-caffeate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-β-glucopyranosyl-(E)-caffeate

There total 9 articles about methyl 4-O-β-glucopyranosyl-(E)-caffeate 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%

methyl 4-[(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl]caffeate → methyl 4-O-β-glucopyranosyl-(E)-caffeate (499-21-8)

Guidance literature:

With sodium methylate; In methanol; for 4h;

DOI:10.1021/jf071205v

Reference yield: 74.0%

methanol (67-56-1) + 3-O-(6-O-(4'-O-(6-O-(4'-O-β-D-glucopyranosyl-(E)-caffeoyl)-β-D-glucopyranosyl)-(E)-caffeoyl)-β-D-glucopyranosyl)-5-O-(6-O-malonyl-β-D-glucopyranosyl)delphinidin trifluoroacetate → delphinidin 3-O-glucoside-5-O-glucoside + 4-O-(β-D-glucopyranosyl)-trans-caffeic acid (147511-61-3) + methyl 4-O-β-glucopyranosyl-(E)-caffeate (499-21-8)

Guidance literature:

With sodium hydroxide; at 0 ℃; for 1h;

DOI:10.1016/j.phytochem.2005.12.024

Reference yield: 36.0%

(E)-3-[4-Hydroxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-4-((E)-2-methoxycarbonyl-vinyl)-phenoxy]-tetrahydro-pyran-2-ylmethyl ester (80585-53-1) → (E)-3-[4-Hydroxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester (80585-55-3) + methyl 4-O-β-glucopyranosyl-(E)-caffeate (499-21-8)

Guidance literature:

With sodium methylate; Product distribution; Ambient temperature; time: overnight;

DOI:10.1016/S0040-4039(01)81866-9

upstream raw materials:

3-hydroxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamic acid ethyl ester

methanol

Platyconin chloride

methyl pentaacetyl-4-O-β-D-glucopyranosylcaffeate

Downstream raw materials:

(E)-3-[3-Hydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-trityloxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid methyl ester

4-O-(β-D-glucopyranosyl)-trans-caffeic acid