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

Base Information

• Chemical Name: 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetamidate
• CAS No.: 697765-24-5
• Molecular Formula: C₅₈H₄₈Cl₃NO₁₈
• Molecular Weight: 1153.37
• Mol file: 697765-24-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetamidate 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:

trichloroacetonitrile (545-06-2) + 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-D-mannopyranose → 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetamidate (697765-24-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2004.01.020

Reference yield:

allyl α-D-mannopyranoside (41308-76-3,821794-45-0) → 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetamidate (697765-24-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Bu₂SnO / methanol / 3 h / Heating

1.2: Bu₄NI / toluene / 16 h / 80 °C

2.1: 7.18 g / pyridine / 20 °C

3.1: 88 percent / ceric ammonium nitrate / toluene; acetonitrile; H₂O / 2 h / 20 °C

4.1: 89 percent / Me₃SiOTf / CH₂Cl₂ / 1 h / 0 °C

5.1: PdCl₂ / methanol / 20 °C

6.1: 1.05 g / DBU / CH₂Cl₂ / 2 h / 20 °C

With pyridine; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In methanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1016/j.carres.2004.01.020

Reference yield:

1,6-di-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranoside (346441-47-2) → 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetamidate (697765-24-5)

Guidance literature:

Multi-step reaction with 5 steps

1: NH₃ / methanol; tetrahydrofuran / 0.75 h

2: 1.47 g / DBU / CH₂Cl₂ / 2 h / 20 °C

3: 89 percent / Me₃SiOTf / CH₂Cl₂ / 1 h / 0 °C

4: PdCl₂ / methanol / 20 °C

5: 1.05 g / DBU / CH₂Cl₂ / 2 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.carres.2004.01.020

upstream raw materials:

trichloroacetonitrile

allyl α-D-mannopyranoside

1,6-di-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranoside

6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate