4-Hydroxy-1-(2-O,3-O,5-O-tribenzoyl-β-D-ribofuranosyl)pyridin-2(1H)-one

Base Information

• Chemical Name: 4-Hydroxy-1-(2-O,3-O,5-O-tribenzoyl-β-D-ribofuranosyl)pyridin-2(1H)-one
• CAS No.: 23220-74-8
• Molecular Formula: C31H25 N O9
• Molecular Weight: 555.541
• Mol file: 23220-74-8.mol

Synonyms:2(1H)-Pyridone,4-hydroxy-1-b-D-ribofuranosyl-,2',3',5'-tribenzoate (8CI); NSC 133121

Chemical Property of 4-Hydroxy-1-(2-O,3-O,5-O-tribenzoyl-β-D-ribofuranosyl)pyridin-2(1H)-one

Chemical Property:

• Vapor Pressure: 4.03E-21mmHg at 25°C
• Melting Point: 140-141 °C
• Boiling Point: 709.4°Cat760mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 382.8°C
• PSA: 130.36000
• Density: 1.43g/cm³
• LogP: 3.75950
• Solubility.: Chloroform, DCM, Methanol

Purity/Quality:

97% ^*data from raw suppliers

4-Hydroxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Hydroxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone is an protected intermediate in the synthesis of 3-Deazauridine (D203240), a structural analog of uridine shown to inhibit the biosynthesis of Cytidine-5''-Triphosphate by competitive inhibition of Cytidine Triphosphate synthetase which is considered to be the primary mode of action of this nucleoside analog.

Technology Process of 4-Hydroxy-1-(2-O,3-O,5-O-tribenzoyl-β-D-ribofuranosyl)pyridin-2(1H)-one

There total 2 articles about 4-Hydroxy-1-(2-O,3-O,5-O-tribenzoyl-β-D-ribofuranosyl)pyridin-2(1H)-one 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:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + 4-hydroxy-2-pyridone (626-03-9) → 4-hydroxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone (23220-74-8)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 130 ℃; for 0.0833333h; microwave irradiation;

DOI:10.1021/jo061885l

Reference yield:

→ 4-hydroxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone (23220-74-8)

Guidance literature:

2,3,5-Tri-O-benzoyl-D-ribofuranosylbromid, 2,4-Bis(trimethylsilyloxy)pyridin;

DOI:10.1039/C1968001547b

Reference yield: 77.0%

4-hydroxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone (23220-74-8) → 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-3,3-difluoropyridine-2,4(1H,3H)-dione (1152256-90-0)

Guidance literature:

With Selectfluor; In acetonitrile; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1021/jm900203h

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

4-hydroxy-2-pyridone

Downstream raw materials:

3-bromo-4-hydroxy-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone

3-deazauridine

1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-3,3-difluoropyridine-2,4(1H,3H)-dione