4-hydroxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Base Information

• Chemical Name: 4-hydroxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS No.: 857500-51-7
• Molecular Formula: C₂₃H₂₈O₁₁
• Molecular Weight: 480.469
• Mol file: 857500-51-7.mol

Synonyms:4-hydroxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Chemical Property of 4-hydroxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-hydroxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

There total 3 articles about 4-hydroxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 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: 57.0%

(p-hydroxyphenyl)boronic acid (71597-85-8) + Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester (10343-15-4,39698-55-0,54400-76-9,78730-32-2,119111-31-8,119111-32-9) → 4-hydroxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (857500-51-7)

Guidance literature:

With copper diacetate; lithium acetate; palladium diacetate; In N,N-dimethyl-formamide; at 100 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2005.04.023

Reference yield:

allyl β-D-glucopyranoside (2595-07-5,7464-56-4,34384-79-7,41308-76-3,48149-72-0,48149-74-2,85249-43-0,119479-69-5,821794-45-0) → 4-hydroxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (857500-51-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 4-N,N-dimethylaminopyridine; pyridine / 1 h / 20 °C

2: 52 percent / copper(II) acetate; lithium acetate; palladium(II) acetate / dimethylformamide / 0.5 h / 80 °C

With pyridine; dmap; lithium acetate; copper diacetate; palladium diacetate; In N,N-dimethyl-formamide; 2: Mizoroki-Heck reaction;

DOI:10.1016/j.tet.2005.08.043

Reference yield:

D-glucose (50-99-7) → 4-hydroxycinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (857500-51-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / immobilized β-D-glucosidase / 72 h / 50 °C

2: 100 percent / 4-N,N-dimethylaminopyridine; pyridine / 1 h / 20 °C

3: 52 percent / copper(II) acetate; lithium acetate; palladium(II) acetate / dimethylformamide / 0.5 h / 80 °C

With pyridine; dmap; immobilized β-D-glucosidase; lithium acetate; copper diacetate; palladium diacetate; In N,N-dimethyl-formamide; 3: Mizoroki-Heck reaction;

DOI:10.1016/j.tet.2005.08.043

upstream raw materials:

(p-hydroxyphenyl)boronic acid

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester

allyl β-D-glucopyranoside

D-glucose

Downstream raw materials:

p-coumaryl alcohol-γ-O-β-D-glucopyranoside