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

Base Information

• Chemical Name: 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranosyl trichloroacetimidate
• CAS No.: 945550-04-9
• Molecular Formula: C₂₉H₂₃Cl₃FNO₈
• Molecular Weight: 638.861
• Mol file: 945550-04-9.mol

Synonyms:2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranosyl trichloroacetimidate

Chemical Property of 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranosyl trichloroacetimidate

There total 6 articles about 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-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: 80.0%

2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranoside (945550-42-5) + trichloroacetonitrile (545-06-2) → 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranosyl trichloroacetimidate (945550-04-9)

Guidance literature:

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

DOI:10.1039/b702961f

Reference yield:

allyl 6-O-triphenylmethyl-2,3,4-tri-O-benzoyl-α-D-mannopyranoside → 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranosyl trichloroacetimidate (945550-04-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / acetic acid; H₂O / 3 h / 70 °C

2: 53 percent / DAST / CH₂Cl₂ / 1.5 h / -40 - 20 °C

3: 89 percent / PdCl₂ / methanol / 4 h / 40 °C

4: 80 percent / DBU / CH₂Cl₂ / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-diaminostilbene-2,2'-disulfonic acid; palladium dichloride; In methanol; dichloromethane; water; acetic acid;

DOI:10.1039/b702961f

Reference yield:

allyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranoside (945550-41-4) → 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranosyl trichloroacetimidate (945550-04-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / PdCl₂ / methanol / 4 h / 40 °C

2: 80 percent / DBU / CH₂Cl₂ / 20 °C

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

DOI:10.1039/b702961f

upstream raw materials:

2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranoside

trichloroacetonitrile

allyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranoside

benzoyl chloride

Downstream raw materials:

benzyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranosyl-(1→3)-2-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

benzyl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranosyl-(1→3)-[2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-α-D-mannopyranosyl-(1→6)]-2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside