Methyl 5-O-feruloylarabinofuranoside

Base Information

• Chemical Name: Methyl 5-O-feruloylarabinofuranoside
• CAS No.: 134796-38-6
• Molecular Formula: C16H20 O8
• Molecular Weight: 340.33
• Nikkaji Number: J507.177A
• Mol file: 134796-38-6.mol

Synonyms:Me-5-FAF;methyl 5-O-feruloylarabinofuranoside;methyl 5-O-trans-feruloyl-alpha-L-arabinofuranoside

Chemical Property of Methyl 5-O-feruloylarabinofuranoside

Chemical Property:

• Vapor Pressure: 3.1E-14mmHg at 25°C
• Boiling Point: 578.7°Cat760mmHg
• Flash Point: 212.4°C
• PSA: 114.68000
• Density: 1.39g/cm³
• LogP: 0.05030
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 340.11581759
• Heavy Atom Count: 24
• Complexity: 440

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(O1)COC(=O)C=CC2=CC(=C(C=C2)O)OC)O)O
• Isomeric SMILES: CO[C@H]1[C@@H]([C@H]([C@@H](O1)COC(=O)/C=C/C2=CC(=C(C=C2)O)OC)O)O

Technology Process of Methyl 5-O-feruloylarabinofuranoside

There total 6 articles about Methyl 5-O-feruloylarabinofuranoside 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: 73.0%

methyl 2,3-di-O-acetyl-5-O-(4'-O-acetylferuloyl)-α-L-arabinofuranoside (142886-56-4) → methyl 5-O-(E)-feruloyl-α-L-arabinofuranoside (134796-38-6)

Guidance literature:

With pyrrolidine; In ethanol; for 48h;

DOI:10.1016/S0008-6215(00)90492-0

Reference yield:

4-acetoxy-3-methoxycinnamoyl chloride (50906-12-2) → methyl 5-O-(E)-feruloyl-α-L-arabinofuranoside (134796-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / pyridine / 5 h

2: 73 percent / pyrrolidine / aq. ethanol / 48 h

With pyrrolidine; pyridine; In ethanol;

DOI:10.1016/S0008-6215(00)90492-0

Reference yield:

methyl 5-O-tert-butyldimethylsilyl-α-L-arabinofuranoside (143003-76-3) → methyl 5-O-(E)-feruloyl-α-L-arabinofuranoside (134796-38-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 5 h

2: 91 percent / 80percent AcOH / 24 h / Ambient temperature

3: 89 percent / pyridine / 5 h

4: 73 percent / pyrrolidine / aq. ethanol / 48 h

With pyrrolidine; pyridine; acetic acid; In ethanol;

DOI:10.1016/S0008-6215(00)90492-0

upstream raw materials:

methyl 2,3-di-O-acetyl-5-O-(4'-O-acetylferuloyl)-α-L-arabinofuranoside

4-acetoxy-3-methoxycinnamoyl chloride

methyl 5-O-tert-butyldimethylsilyl-α-L-arabinofuranoside

methyl 2,3-di-O-acetyl-α-L-arabinofuranoside

Downstream raw materials:

methyl 5-O-<4-O-<2-(4-acetoxy-3-methoxyphenyl)-2-hydroxy-1-(hydroxymethyl)ethyl>feruloyl>-α-L-arabinofuranoside

methyl 5-O-<4-O-<2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-(hydroxymethyl)ethyl>feruloyl>-α-L-arabinofuranoside

(E)-3-{4-[3-Acetoxy-1-(4-acetoxy-3-methoxy-phenyl)-2-(2-methoxy-phenoxy)-propoxy]-3-methoxy-phenyl}-acrylic acid (2S,3S,4R,5R)-3,4-diacetoxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

(E)-3-{4-[3-Acetoxy-1-(4-acetoxy-3-methoxy-phenyl)-2-(2-methoxy-phenoxy)-propoxy]-3-methoxy-phenyl}-acrylic acid (2S,3S,4R,5R)-3,4-diacetoxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

Refernces