3-O-benzoyl-2,4-diazido-2,4,6-trideoxy-α-D-galactopyranoside trichloroacetimidate

Base Information

• Chemical Name: 3-O-benzoyl-2,4-diazido-2,4,6-trideoxy-α-D-galactopyranoside trichloroacetimidate
• CAS No.: 1432492-28-8
• Molecular Formula: C₁₅H₁₄Cl₃N₇O₄
• Molecular Weight: 462.68
• Mol file: 1432492-28-8.mol

Synonyms:3-O-benzoyl-2,4-diazido-2,4,6-trideoxy-α-D-galactopyranoside trichloroacetimidate

Chemical Property of 3-O-benzoyl-2,4-diazido-2,4,6-trideoxy-α-D-galactopyranoside trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzoyl-2,4-diazido-2,4,6-trideoxy-α-D-galactopyranoside trichloroacetimidate

There total 8 articles about 3-O-benzoyl-2,4-diazido-2,4,6-trideoxy-α-D-galactopyranoside trichloroacetimidate 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: 85.0%

C13H14N6O4 + trichloroacetonitrile (545-06-2) → 3-O-benzoyl-2,4-diazido-2,4,6-trideoxy-α-D-galactopyranoside trichloroacetimidate (1432492-28-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -5 ℃; for 1h; Inert atmosphere;

DOI:10.1039/c3ob40615f

Reference yield:

phenyl 6-deoxy-1-thio-β-D-mannopyranoside (1432492-22-2) → 3-O-benzoyl-2,4-diazido-2,4,6-trideoxy-α-D-galactopyranoside trichloroacetimidate (1432492-28-8)

Guidance literature:

Multi-step reaction with 5 steps

1: dimethyltin dichloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / Inert atmosphere

2: pyridine / dichloromethane / 2 h / -10 - 10 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 8 h / 20 °C / Inert atmosphere

4: N-Bromosuccinimide / tetrahydrofuran; water / 0.67 h / 0 - 20 °C / Inert atmosphere

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / -5 °C / Inert atmosphere

With pyridine; N-Bromosuccinimide; sodium azide; dimethyltin dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c3ob40615f

Reference yield:

phenyl-1-thio-β-D-mannopyranoside (77481-63-1) → 3-O-benzoyl-2,4-diazido-2,4,6-trideoxy-α-D-galactopyranoside trichloroacetimidate (1432492-28-8)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 6 h / 0 - 20 °C / Inert atmosphere

2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 80 °C / Inert atmosphere

3: dimethyltin dichloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / Inert atmosphere

4: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 2 h / -10 - 10 °C / Inert atmosphere

5: sodium azide / N,N-dimethyl-formamide / 8 h / 20 °C / Inert atmosphere

6: N-Bromosuccinimide / tetrahydrofuran; water / 0.67 h / 0 - 20 °C / Inert atmosphere

7: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / -5 °C / Inert atmosphere

With pyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; sodium azide; trifluoromethylsulfonic anhydride; dimethyltin dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c3ob40615f

upstream raw materials:

phenyl-1-thio-β-D-mannopyranoside

phenyl 6-O-tosyloxy-1-thio-β-D-mannopyranoside

benzoyl chloride

phenyl 6-deoxy-1-thio-β-D-mannopyranoside