Benzyl 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: Benzyl 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS No.: 4171-69-1
• Molecular Formula: C₃₆H₃₉NO₆
• Molecular Weight: 581.709
• Mol file: 4171-69-1.mol

Synonyms:Benzyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of Benzyl 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property:

• Melting Point: 167-168°C
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform

Purity/Quality:

95% ^*data from raw suppliers

Benzyl2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Benzyl 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside is a reactant used in the preparation of oligosaccharide and glucosamine containing peptides used as inhibitors of influenza virus neuraminidase.

Technology Process of Benzyl 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 21 articles about Benzyl 2-Acetamido-3,4,6-tri-O-benzyl-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: 84.0%

2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl acetate (65760-01-2) + benzyl alcohol (100-51-6,185532-71-2) → Benzyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (4171-69-1)

Guidance literature:

With bismuth(lll) trifluoromethanesulfonate; In dichloromethane; at 45 ℃; for 3h;

DOI:10.1021/acs.joc.6b02305

Reference yield: 82.0%

1,3,4,6-tetra-O-benzyl-2-deoxy-2-diglycolylimido-β-D-glucopyranoside (871116-05-1) → Benzyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (4171-69-1)

Guidance literature:

1,3,4,6-tetra-O-benzyl-2-deoxy-2-diglycolylimido-β-D-glucopyranoside; With potassium hydroxide; In ethanol; for 4h; Heating;

With pyridine; acetic anhydride; at 20 ℃;

DOI:10.1002/ejoc.200500107

Reference yield: 69.0%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + N-Trimethylsilylacetamide (13435-12-6) + benzyl alcohol (100-51-6,185532-71-2) → Benzyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (4171-69-1)

Guidance literature:

3,4,6-tri-O-benzyl-D-glucal; N-Trimethylsilylacetamide; With thianthrene-5-oxide; trifluoromethylsulfonic anhydride; N,N-diethylaniline; In dichloromethane; chloroform; at 23 ℃; for 2h;

benzyl alcohol; With Amberlyst-15 acidic resin; In dichloromethane; chloroform;

DOI:10.1002/(SICI)1521-3773(20000103)39:1<204::AID-ANIE204>3.0.CO;2-Z

upstream raw materials:

N-Acetyl-D-glucosamine

benzyl bromide

benzyl 2-Amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

acetic anhydride

Downstream raw materials:

3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose

benzyl 2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

2-amino-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose

2-benzamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose