2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
• CAS No.: 500217-09-4
• Molecular Formula: C₆₃H₅₀Cl₃NO₁₈
• Molecular Weight: 1215.44
• Mol file: 500217-09-4.mol

Synonyms:2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate

Chemical Property of 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate

There total 10 articles about 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl 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: 90.0%

trichloroacetonitrile (545-06-2) + 3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2,4,6-tri-O-benzoyl-α-D-mannopyranose (500217-07-2) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (500217-09-4)

Guidance literature:

With potassium carbonate; In dichloromethane;

DOI:10.1081/CAR-120014899

Reference yield:

p-methoxyphenyl α-D-mannopyranoside (28541-75-5,12167-34-9) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (500217-09-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Bu₂SnO / methanol / 2 h / Heating

1.2: 65 percent / Bu₄NI / benzene / 24 h / 60 °C

2.1: 100 percent / pyridine / 20 °C

3.1: 90 percent / PdCl₂ / methanol / 40 °C

4.1: 85 percent / TMSOTf / CH₂Cl₂ / 3 h / -25 - 20 °C

5.1: 80 percent / (NH₄)2Ce(NO₃)6 / acetonitrile; H₂O / 0.5 h / 20 °C

6.1: 90 percent / K₂CO₃ / CH₂Cl₂

With pyridine; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; di(n-butyl)tin oxide; potassium carbonate; palladium dichloride; In methanol; dichloromethane; water; acetonitrile;

DOI:10.1081/CAR-120014899

Reference yield:

p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside (319922-17-3) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1-> 3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (500217-09-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / pyridine / 20 °C

2: 90 percent / PdCl₂ / methanol / 40 °C

3: 85 percent / TMSOTf / CH₂Cl₂ / 3 h / -25 - 20 °C

4: 80 percent / (NH₄)2Ce(NO₃)6 / acetonitrile; H₂O / 0.5 h / 20 °C

5: 90 percent / K₂CO₃ / CH₂Cl₂

With pyridine; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; palladium dichloride; In methanol; dichloromethane; water; acetonitrile;

DOI:10.1081/CAR-120014899

upstream raw materials:

trichloroacetonitrile

3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-2,4,6-tri-O-benzoyl-α-D-mannopyranose

benzoyl chloride

C₄₀H₃₈O₁₅