2-acetoxy-4-methoxy-6-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)acetophenone

Base Information

• Chemical Name: 2-acetoxy-4-methoxy-6-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)acetophenone
• CAS No.: 169566-42-1
• Molecular Formula: C₄₅H₄₆O₁₀
• Molecular Weight: 746.854
• Mol file: 169566-42-1.mol

Synonyms:2-acetoxy-4-methoxy-6-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)acetophenone

Chemical Property of 2-acetoxy-4-methoxy-6-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)acetophenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-acetoxy-4-methoxy-6-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)acetophenone

There total 1 articles about 2-acetoxy-4-methoxy-6-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)acetophenone 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: 52.0%

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride (89025-46-7) + 2-acetylphloroglucinol 3-acetate-5-methyl ether → 2-acetoxy-4-methoxy-6-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)acetophenone (169566-42-1)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -20 - 20 ℃;

DOI:10.1246/bcsj.68.1379

Reference yield:

2-acetoxy-4-methoxy-6-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)acetophenone (169566-42-1) → Acetic acid 2-acetyl-5-methoxy-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl ester

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate; for 36h; Ambient temperature;

DOI:10.1246/bcsj.68.1379

Reference yield:

2-acetoxy-4-methoxy-6-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)acetophenone (169566-42-1) → 2-acetoxy-4-methoxy-6-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)acetophenone

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / ethyl acetate; ethanol / 36 h / Ambient temperature

2: 4-dimethylaminopyridine, pyridine / 16 h / Ambient temperature

With pyridine; dmap; hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate;

DOI:10.1246/bcsj.68.1379

upstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride