O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose

Base Information

• Chemical Name: O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose
• CAS No.: 53942-45-3
• Molecular Formula: C40H57N3O24
• Molecular Weight: 963.898
• Mol file: 53942-45-3.mol

Synonyms:O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose;Tri-N-acetyl Chitotriose Octaacetate;O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy--D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy--D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose

Chemical Property of O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 315 °C
• Refractive Index: 1.533
• Boiling Point: 1018.947°C at 760 mmHg
• PKA: 13.46±0.70(Predicted)
• Flash Point: 570.038°C
• PSA: 343.85000
• Density: 1.387g/cm³
• LogP: -1.40250

Purity/Quality:

99% ^*data from raw suppliers

ChitotrioseUndecaacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: An intermediate of 4-Methylumbelliferyl -D-N,N?N?Triacetylchitotrioside An intermediate of 4-Methylumbelliferyl β-D-N,N',N”-Triacetylchitotrioside. An intermediate of 4-Methylumbelliferyl β-D-N,N'',N”-Triacetylchitotrioside.

Technology Process of O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-D-glucopyranose

There total 2 articles about O-3,4,6-Tri-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-O-3,6-di-O-acetyl-2-(acetylamino)-2-deoxy-b-D-glucopyranosyl-(1-4)-2-(acetylamino)-2-deoxy-1,3,6-triacetate-a-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: 6.1%

acetic anhydride (108-24-7) → acetyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranose (53942-46-4,117399-51-6) + (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose (53942-45-3) + chitobiose octaacetate (7284-18-6)

Guidance literature:

With sulfuric acid; 1.) room temperature; 2.) 55 deg C, 3h;

Reference yield:

acetic anhydride (108-24-7) + chitosan (9012-76-4) → acetyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-acetyl-2-deoxy-α-D-glucopyranose (53942-46-4,117399-51-6) + (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose (53942-45-3) + chitobiose octaacetate (7284-18-6)

Guidance literature:

chitosan; With hydrogenchloride; chitosanase; In water; at 50 ℃; for 24h; pH=6; Enzymatic reaction;

acetic anhydride; With sulfuric acid; at 50 ℃; for 8h; Overall yield = > 60 %;

DOI:10.3390/md13031267

Reference yield:

(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranose (53942-45-3) → tert-butyldiphenylsilyl (3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-trifluoroacetamido-β-D-glucopyranosyl)-(1→4)-(3,6-di-O-acetyl-2-deoxy-2-trifluoroacetamido-β-D-glucopyranosyl)-(1→4)-3,6-di-O-acetyl-2-deoxy-2-trifluoroacetamido-β-D-glucopyranoside

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 0.33 h / 135 °C / Inert atmosphere; Sealed tube

2: hydrazinium monoacetate / N,N-dimethyl-formamide / 55 °C / Inert atmosphere

3: 1H-imidazole / N,N-dimethyl-formamide / 40 h / 20 °C / Inert atmosphere

4: sodium methylate / methanol / 20 °C / Inert atmosphere

5: zinc(II) chloride / 1 h / 20 °C / Inert atmosphere

6: pyridine / 48 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; sodium methylate; hydrazinium monoacetate; zinc(II) chloride; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/anie.201406802

upstream raw materials:

acetic anhydride

chitosan

Downstream raw materials:

4-methylumbelliferyl β-D-N,N′,N′′-triacetylchitotrioside

Refernces

• 1、 Inaba, Toyoaki,Ohgushi, Tadayasu,Iga, Yoshiro,Hasegawa, Eiichi. "Synthesis of 4-Methylcoumarin-7-yloxy Tetra-N-acetyl-β-chitotetraoside, a Novel Synthetic Substrate for the Fluorometric Assay of Lysozyme". . p. 1597 - 1603. Retrieved 2007/10/02.