2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside

Base Information

• Chemical Name: 2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside
• CAS No.: 1446474-57-2
• Molecular Formula: C₅₂H₅₇N₃O₁₄
• Molecular Weight: 948.036
• Mol file: 1446474-57-2.mol

Synonyms:2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside

Chemical Property of 2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside

There total 6 articles about 2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside 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: 65.0%

S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside (403646-50-4) + 2-azidoethyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside (653597-40-1) → 2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside (1446474-57-2)

Guidance literature:

S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 ℃; for 0.5h; molecular sieves; Inert atmosphere;

2-azidoethyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside; In dichloromethane; at -78 ℃; for 2h; molecular sieves; Inert atmosphere;

With triethylamine; In dichloromethane;

Reference yield:

phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside (168138-26-9) → 2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside (1446474-57-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 4 h / 20 °C

2.1: trimethylsilyl trifluoromethanesulfonate; N-iodo-succinimide / dichloromethane / 2 h / -40 °C / molecular sieves; Inert atmosphere

3.1: sodium methylate; methanol / 2 h / 20 °C

3.2: Dowex_.(R). 50WX₈-100 (H⁺)

4.1: trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; 1-benzenesulfinyl piperidine / dichloromethane / 0.5 h / -60 °C / molecular sieves; Inert atmosphere

4.2: 2 h / -78 °C / molecular sieves; Inert atmosphere

With pyridine; methanol; N-iodo-succinimide; 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; sodium methylate; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane;

Reference yield:

2-azidoethanol (1517-05-1) + phenyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-α-D-mannopyranoside (1446474-52-7) → 2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside (1446474-57-2) + 2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-β-D-mannopyranoside (1446474-53-8)

Guidance literature:

phenyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-α-D-mannopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

2-azidoethanol; In dichloromethane; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1002/chem.201203963

upstream raw materials:

S-phenyl 4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-1-thio-α-D-mannnopyranoside

2-azidoethyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside

phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside

phenyl 2-O-acetyl-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-α-D-mannopyranoside