2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxymannopyranose

Base Information

• Chemical Name: 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxymannopyranose
• CAS No.: 76375-61-6
• Molecular Formula: C₁₆H₂₃NO₁₀
• Molecular Weight: 389.359
• Nikkaji Number: J3.032.305J
• ChEMBL ID: CHEMBL492064
• Mol file: 76375-61-6.mol

Synonyms:2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxymannopyranose;Ac4-NAcMan

Chemical Property of 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxymannopyranose

Chemical Property:

• Vapor Pressure: 2.53E-11mmHg at 25°C
• Boiling Point: 530.2°C at 760 mmHg
• Flash Point: 274.4°C
• Density: 1.3g/cm³
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 389.13219593
• Heavy Atom Count: 27
• Complexity: 604

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)N[C@H]1[C@H]([C@@H]([C@H](OC1OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxymannopyranose

There total 124 articles about 2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxymannopyranose 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: 95.0%

2-amino-2-deoxy-D-glucose hydrochloride + acetic anhydride (108-24-7) → 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3)

Guidance literature:

With pyridine; at 20 ℃; Cooling with ice;

DOI:10.1080/07328303.2014.996290

Reference yield: 90.0%

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2,10034-19-2,10034-20-5,34948-62-4,110253-00-4,1191127-63-5) + acetic anhydride (108-24-7) → 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3)

Guidance literature:

With pyridine;

DOI:10.1002/ejoc.201200062

Reference yield: 88.0%

N-acetyl-D-glucosamine (14131-68-1) + acetic anhydride (108-24-7) → 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3)

Guidance literature:

With pyridine; at 20 ℃; for 29.5h;

upstream raw materials:

acetic anhydride

2-amino-2-deoxy-D-idose; hydrochloride

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride

D-(+)-glucosamine hydrochloride

Downstream raw materials:

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline

propyl 2-acetamido-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

O-(N-acetamido-2-tri-O-acetyl-3,4,6-desoxy-2-β-D-glucopyranosyl)-4-O-acetyl-1-tri-O-benzyl-2,3,5-D-ribitol

ethyl 2-acetamido-3,4,6-tetra-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside

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