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

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate
• CAS No.: 612057-06-4
• Molecular Formula: C₅₃H₄₆Cl₃NO₁₈
• Molecular Weight: 1091.3
• Mol file: 612057-06-4.mol

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

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

There total 7 articles about 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-acetyl-2-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: 83.1%

trichloroacetonitrile (545-06-2) + allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-mannopyranoside (612057-05-3) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (612057-06-4)

Guidance literature:

allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-mannopyranoside; With sodium acetate; palladium dichloride; In water; acetic acid; for 12h;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 12h;

DOI:10.1016/S0008-6215(03)00267-2

Reference yield:

benzoyl chloride (98-88-4) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (612057-06-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88.1 percent / pyridine / 12 h / 20 °C

2.1: trifluoroacetic acid; H₂O / 2 h / 20 °C

3.1: pyridine / 12 h / 20 °C

4.1: AcONa; PdCl₂ / acetic acid; H₂O / 12 h

4.2: 83.1 percent / DBU / CH₂Cl₂ / 12 h

With sodium acetate; palladium dichloride; In pyridine; water; acetic acid; trifluoroacetic acid;

DOI:10.1016/S0008-6215(03)00267-2

Reference yield:

allyl 4,6-di-O-benzylidene-α-D-mannopyranoside (81600-93-3) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (612057-06-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 76.3 percent / TMSOTf / CH₂Cl₂ / 2 h / -20 °C

2.1: 88.1 percent / pyridine / 12 h / 20 °C

3.1: trifluoroacetic acid; H₂O / 2 h / 20 °C

4.1: pyridine / 12 h / 20 °C

5.1: AcONa; PdCl₂ / acetic acid; H₂O / 12 h

5.2: 83.1 percent / DBU / CH₂Cl₂ / 12 h

With trimethylsilyl trifluoromethanesulfonate; sodium acetate; palladium dichloride; In pyridine; dichloromethane; water; acetic acid; trifluoroacetic acid;

DOI:10.1016/S0008-6215(03)00267-2

upstream raw materials:

trichloroacetonitrile

allyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-mannopyranoside

benzoyl chloride

allyl 4,6-di-O-benzylidene-α-D-mannopyranoside