4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-benzaldehyde

Base Information

• Chemical Name: 4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-benzaldehyde
• CAS No.: 696611-06-0
• Molecular Formula: C₂₁H₂₄O₁₁
• Molecular Weight: 452.415
• Mol file: 696611-06-0.mol

Synonyms:4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-benzaldehyde

Chemical Property of 4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-benzaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-benzaldehyde

There total 1 articles about 4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-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: 41.0%

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) + acetobromomannose (13242-53-0) → 4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-benzaldehyde (696611-06-0)

Guidance literature:

With silver(l) oxide; In acetonitrile; for 1h; Heating;

DOI:10.1002/anie.200600808

Reference yield: 82.0%

4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-benzaldehyde (696611-06-0) → 4-(hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (912281-46-0,105054-56-6)

Guidance literature:

With sodium tetrahydroborate; silica gel; In chloroform; isopropyl alcohol; at 0 - 20 ℃;

DOI:10.1002/anie.200600808

Reference yield:

4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-benzaldehyde (696611-06-0) → 4-[4-(α-D-mannopyranosyloxy)-benzyloxycarbonyl]amino-5-(methylsulfanyl)cyclopentane-1,2,3-triol (912281-41-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / sodium borohydride; silica gel / propan-2-ol; CHCl₃ / 0 - 20 °C

2: 90 percent / pyridine / CH₂Cl₂ / 18 h / 20 °C

3: 83 percent / triethylamine / dimethylformamide / 18 h / 20 °C

4: 94 percent / ammonia / methanol / 5 h / 0 °C

With pyridine; sodium tetrahydroborate; ammonia; silica gel; triethylamine; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1002/anie.200600808

upstream raw materials:

4-hydroxy-benzaldehyde

acetobromomannose

Downstream raw materials:

4-(hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

4-[4-(α-D-mannopyranosyloxy)-benzyloxycarbonyl]amino-5-(methylsulfanyl)cyclopentane-1,2,3-triol

5-[4-(α-D-mannopyranosyloxy)-benzyloxycarbonyl]amino-1,2,3,4-cyclopentanetetrol

4-(4-nitro-phenoxycarbonyloxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside