(+)-4-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-Dglucopyranosyloxy)benzaldehyde

Base Information

• Chemical Name: (+)-4-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-Dglucopyranosyloxy)benzaldehyde
• CAS No.: 139933-35-0
• Molecular Formula: C₃₃H₄₀O₁₉
• Molecular Weight: 740.669
• Mol file: 139933-35-0.mol

Synonyms:(+)-4-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-Dglucopyranosyloxy)benzaldehyde

Chemical Property of (+)-4-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-Dglucopyranosyloxy)benzaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-4-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-Dglucopyranosyloxy)benzaldehyde

There total 5 articles about (+)-4-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-Dglucopyranosyloxy)benzaldehyde 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: 88.0%

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) + 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide (4753-07-5) → (+)-4-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-Dglucopyranosyloxy)benzaldehyde (139933-35-0)

Guidance literature:

With benzyltri(n-butyl)ammonium chloride; potassium carbonate; In chloroform; at 20 ℃; for 24h;

DOI:10.1039/c9ob01076a

Reference yield: 37.0%

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl bromide (70223-97-1) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → (+)-4-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-Dglucopyranosyloxy)benzaldehyde (139933-35-0)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In chloroform; water; at 45 ℃;

DOI:10.1016/j.ejmech.2007.03.018

Reference yield:

lactose octaacetate (34213-32-6) → (+)-4-(4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2,3,6-tri-O-acetyl-Dglucopyranosyloxy)benzaldehyde (139933-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1: bismuth(III) bromide; trimethylsilyl bromide / dichloromethane / 15 h / 20 °C / Inert atmosphere

2: benzyltri(n-butyl)ammonium chloride; potassium carbonate / chloroform / 24 h / 20 °C

With trimethylsilyl bromide; benzyltri(n-butyl)ammonium chloride; bismuth(III) bromide; potassium carbonate; In dichloromethane; chloroform;

DOI:10.1039/c9ob01076a

upstream raw materials:

4-hydroxy-benzaldehyde

2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl bromide

2,3,6-tetra-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-glucopyranosylbromide

Downstream raw materials:

C₃₄H₄₃NO₁₉

C₃₃H₄₁NO₁₉

N-phenyl-C-4-(2,3,4,6,2',3',6'-hepta-O-acetyl-β-D-lactosyloxy)phenyl nitrone