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

Base Information

• Chemical Name: 2,3,4-tri-O-benzoyl-6-O-diphenylphosphoryl-α-D-mannopyranosyl trichloroacetimidate
• CAS No.: 815589-22-1
• Molecular Formula: C₄₁H₃₃Cl₃NO₁₂P
• Molecular Weight: 869.045
• Mol file: 815589-22-1.mol

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

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

There total 7 articles about 2,3,4-tri-O-benzoyl-6-O-diphenylphosphoryl-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) + 2,3,4-tri-O-benzoyl-6-O-diphenylphosphoryl-α-D-mannopyranose (815589-20-9) → 2,3,4-tri-O-benzoyl-6-O-diphenylphosphoryl-α-D-mannopyranosyl trichloroacetimidate (815589-22-1)

Guidance literature:

With potassium carbonate; In 1,2-dichloro-ethane; at 0 ℃; for 0.166667h;

DOI:10.1016/j.bmc.2004.09.005

Reference yield:

chlorophosphoric acid diphenyl ester (2524-64-3) → 2,3,4-tri-O-benzoyl-6-O-diphenylphosphoryl-α-D-mannopyranosyl trichloroacetimidate (815589-22-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / 1,2-dichloro-ethane / 0 - 20 °C

2: 64 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 0.17 h / 30 °C

3: 90 percent / K₂CO₃ / 1,2-dichloro-ethane / 0.17 h / 0 °C

With ammonium cerium(IV) nitrate; potassium carbonate; In water; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/j.bmc.2004.09.005

Reference yield:

(2R,3S,4S,5S,6S)-2-Hydroxymethyl-6-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4,5-triol → 2,3,4-tri-O-benzoyl-6-O-diphenylphosphoryl-α-D-mannopyranosyl trichloroacetimidate (815589-22-1)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 0 - 20 °C

2: 1,2-dichloro-ethane / 0 - 20 °C

3: 710 mg / p-TsOH*H₂O / methanol; acetonitrile / 0.17 h / 70 °C

4: 93 percent / 1,2-dichloro-ethane / 0 - 20 °C

5: 64 percent / cerium(IV) ammonium nitrate / acetonitrile; H₂O / 0.17 h / 30 °C

6: 90 percent / K₂CO₃ / 1,2-dichloro-ethane / 0.17 h / 0 °C

With pyridine; ammonium cerium(IV) nitrate; potassium carbonate; toluene-4-sulfonic acid; In methanol; water; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/j.bmc.2004.09.005

upstream raw materials:

trichloroacetonitrile

2,3,4-tri-O-benzoyl-6-O-diphenylphosphoryl-α-D-mannopyranose

chlorophosphoric acid diphenyl ester

Downstream raw materials:

methyl 3-O-(2,3,4-tri-O-benzoyl-6-O-diphenylphosphoryl-α-D-mannopyranosyl)-2,4,6-tri-O-benzoyl-α-D-mannopyranoside

benzyl 2-O-(2,3,4-tri-O-benzoyl-6-O-diphenylphosphoryl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside