phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside

Base Information

• Chemical Name: phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside
• CAS No.: 548477-84-5
• Molecular Formula: C₅₃H₄₅N₃O₁₃Se
• Molecular Weight: 1010.91
• Mol file: 548477-84-5.mol

Synonyms:phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside

Chemical Property of phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside

There total 1 articles about phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside 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: 56.0%

2,3,5,6-tetra-O-benzoyl-D-galactofuranose (5531-48-6,5531-49-7,5531-50-0,5595-67-5,5636-01-1,108223-94-5) + phenyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside (167074-40-0) → phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside (548477-84-5)

Guidance literature:

2,3,5,6-tetra-O-benzoyl-D-galactofuranose; With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 - -40 ℃;

phenyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside; In dichloromethane; at -40 - 20 ℃;

DOI:10.1021/ol034528v

Reference yield: 65.0%

isopropyl 2-O-benzoyl-4,6-O-[1-(R)-(methoxycarbonyl)-ethylidene]-β-D-galactopyranoside (936324-85-5) + phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside (548477-84-5) → isopropyl 2-O-benzoyl-3-O-[2-azido-4,6-O-benzylidene-3-O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-2-deoxy-α-D-galactopyranosyl]-4,6-O-[1-(R)-(methoxycarbonyl)-ethylidene]-β-D-galactopyranoside (936324-90-2)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.tetlet.2007.02.067

Reference yield:

phenyl 3-O-(2,3,5,6-tetra-O-benzoyl-α-D-galactofuranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside (548477-84-5) → C69H69O23N

Guidance literature:

Multi-step reaction with 2 steps

1.1: 65 percent / NIS; TMSOTf / CH₂Cl₂ / 1 h / 0 - 20 °C

2.1: Me₃P / toluene / 16 h

2.2: pyridine / 16 h

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; trimethylphosphane; In dichloromethane; toluene;

DOI:10.1016/j.tetlet.2007.02.067

upstream raw materials:

2,3,5,6-tetra-O-benzoyl-D-galactofuranose

phenyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-1-seleno-α-D-galactopyranoside

Downstream raw materials:

isopropyl 2-O-benzoyl-3-O-[2-azido-4,6-O-benzylidene-3-O-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-2-deoxy-α-D-galactopyranosyl]-4,6-O-[1-(R)-(methoxycarbonyl)-ethylidene]-β-D-galactopyranoside

isopropyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->3)-2-azido-6-O-benzyl-2-deoxy-α-D-galactopyranosyl-(1->3)-2-O-benzoyl-4,6-O-[1-(R)-(methoxycarbonyl)-ethylidene]-β-D-galactopyranoside