3,4,6-Tri-o-acetyl-2-deoxy-2-[(trifluoroacetyl)amino]hexopyranose

Base Information

• Chemical Name: 3,4,6-Tri-o-acetyl-2-deoxy-2-[(trifluoroacetyl)amino]hexopyranose
• CAS No.: 28719-30-4
• Molecular Formula: C14H18 F3 N O9
• Molecular Weight: 401.2892
• NSC Number: 140392
• DSSTox Substance ID: DTXSID50301019
• Mol file: 28719-30-4.mol

Synonyms:3,4,6-tri-o-acetyl-2-deoxy-2-[(trifluoroacetyl)amino]hexopyranose;28719-30-4;NSC140392;DTXSID50301019;NNBSYZWMCHTYJQ-UHFFFAOYSA-N;NSC-140392

Chemical Property of 3,4,6-Tri-o-acetyl-2-deoxy-2-[(trifluoroacetyl)amino]hexopyranose

Chemical Property:

• Vapor Pressure: 1.94E-11mmHg at 25°C
• Boiling Point: 484.9°C at 760 mmHg
• Flash Point: 247.1°C
• Density: 1.44g/cm³
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 8
• Exact Mass: 401.09336564
• Heavy Atom Count: 27
• Complexity: 595

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)O)NC(=O)C(F)(F)F)OC(=O)C)OC(=O)C

Technology Process of 3,4,6-Tri-o-acetyl-2-deoxy-2-[(trifluoroacetyl)amino]hexopyranose

There total 4 articles about 3,4,6-Tri-o-acetyl-2-deoxy-2-[(trifluoroacetyl)amino]hexopyranose 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: 50.0%

3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucospyranosyl bromide (6736-63-6) → 3,4,6-Tri-O-acetyl-2-trifluoracetamino-2-desoxy-D-glucose (28719-30-4) + 2-trifluoromethyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranose)-[1,2,d]-2-oxazoline (28719-31-5)

Guidance literature:

With Tetrakis(dimethylamino)ethylen; In tetrahydrofuran; at 20 ℃; for 5h; Reagent/catalyst; Inert atmosphere; UV-irradiation;

DOI:10.1016/j.tet.2013.09.032

Reference yield: 38.0%

3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucospyranosyl bromide (6736-63-6) → 3,4,6-Tri-O-acetyl-2-trifluoracetamino-2-desoxy-D-glucose (28719-30-4) + C14H18F3NO8

Guidance literature:

With sodium tetraphenyl borate; In tetrahydrofuran; for 4.5h; Inert atmosphere; UV-irradiation;

DOI:10.1016/j.tet.2013.09.032

Reference yield: 36.0%

3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucospyranosyl bromide (6736-63-6) → 3,4,6-Tri-O-acetyl-2-trifluoracetamino-2-desoxy-D-glucose (28719-30-4) + C14H18F3NO8 + 2-trifluoromethyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranose)-[1,2,d]-2-oxazoline (28719-31-5)

Guidance literature:

With Tetrakis(dimethylamino)ethylen; In tetrahydrofuran; for 1.5h; Inert atmosphere; UV-irradiation; Cooling with ice;

DOI:10.1016/j.tet.2013.09.032

upstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucospyranosyl bromide

Downstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetylamino-α-D-glucopyranosyl dibenzyl phosphate

uridine 5'-(2-amino-2-deoxy-α-D-glucopyranosyl)-diphosphate