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

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-β-D-glucopyranose
• CAS No.: 182822-89-5
• Molecular Formula: C₂₉H₃₃NO₆
• Molecular Weight: 491.584
• Mol file: 182822-89-5.mol

Synonyms:3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-β-D-glucopyranose

Chemical Property of 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-β-D-glucopyranose

There total 4 articles about 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-β-D-glucopyranose 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:

N-((3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yl)acetamide (91927-50-3) → 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-β-D-glucopyranose (182822-89-5) + 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose (121123-45-3)

Guidance literature:

With [10%-Pd/Al₂O₃]; ammonium formate; In methanol; at 20 ℃; for 6h; optical yield given as %de; regioselective reaction;

DOI:10.1016/j.tetlet.2011.09.130

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) → 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-β-D-glucopyranose (182822-89-5) + 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose (121123-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide

2: [10%-Pd/Al₂O₃]; ammonium formate / methanol / 6 h / 20 °C

With [10%-Pd/Al₂O₃]; ammonium formate; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2011.09.130

Reference yield:

benzyl bromide (100-39-0) → 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-β-D-glucopyranose (182822-89-5) + 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose (121123-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide

2: [10%-Pd/Al₂O₃]; ammonium formate / methanol / 6 h / 20 °C

With [10%-Pd/Al₂O₃]; ammonium formate; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2011.09.130

upstream raw materials:

N-((3R,4R,5S,6R)-2,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-3-yl)acetamide

N-Acetyl-D-glucosamine

benzyl bromide