methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside
• CAS No.: 269065-36-3
• Molecular Formula: C₂₃H₂₅NO₈
• Molecular Weight: 443.453
• Mol file: 269065-36-3.mol

Synonyms:methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside

Chemical Property of methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside

There total 5 articles about methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside 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: 82.4%

benzoyl chloride (98-88-4) + methyl 2-acetylamido-2-deoxy-D-glucoside (6082-04-8) → methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside (269065-36-3)

Guidance literature:

With pyridine; at 20 ℃; for 15h;

DOI:10.1016/S0008-6215(99)00314-6

Reference yield: 69.0%

methyl N-acetyl-D-glucosamine (3055-46-7,3946-01-8,5627-24-7,6082-04-8,6082-22-0,17327-09-2,22256-76-4,32087-35-7,32087-36-8,95341-97-2,114029-61-7,114612-10-1,114612-13-4,116559-74-1) + benzoyl chloride (98-88-4) → methyl 2-acetamido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-glucopyranoside (1370586-92-7) + methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside (176690-90-7) + methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside (269065-36-3)

Guidance literature:

With pyridine; at -40 - 20 ℃; for 4.5h; Inert atmosphere;

DOI:10.1002/adsc.201100735

Reference yield:

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) → methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside (269065-36-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 63.5 percent / AcCl / 5 h / Heating

2: triethyl orthoformate; TsOH / acetonitrile / 2 h / 20 °C

3: pyridine / 20 °C

4: HOAc / H₂O / 6 h / Heating

5: 305 mg / pyridine / 20 °C

With pyridine; toluene-4-sulfonic acid; acetic acid; acetyl chloride; orthoformic acid triethyl ester; In water; acetonitrile;

DOI:10.1016/j.carres.2003.09.030

upstream raw materials:

benzoyl chloride

methyl 2-acetylamido-2-deoxy-D-glucoside

methyl 2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside

N-Acetyl-D-glucosamine

Downstream raw materials:

methyl 2-acetamido-3,6-di-O-benzoyl-2,4-dideoxy-α-D-xylo-hexopyranoside

methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside

methyl 4,6-di-O-acetyl-2,3-di-O-benzoyl-α-D-mannopyranosyl-(1-> 4)-2-acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside

methyl 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-4-fluoro-α-D-glucopyranoside