2,3-DI-O-Benzoyluridine

Base Information

• Chemical Name: 2,3-DI-O-Benzoyluridine
• CAS No.: 50408-20-3
• Molecular Formula: C23H20 N2 O8
• Molecular Weight: 452.42
• European Community (EC) Number: 256-581-8
• Mol file: 50408-20-3.mol

Synonyms:2,3-DI-O-BENZOYLURIDINE;50408-20-3;Oprea1_348993;AKOS037655818;SS-5159;FT-0639899;4-(benzoyloxy)-2-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-5-(hydroxymethyl)oxolan-3-yl benzoate

Chemical Property of 2,3-DI-O-Benzoyluridine

Chemical Property:

• PSA: 136.92000
• Density: 1.48g/cm³
• LogP: 0.87750
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 452.12196560
• Heavy Atom Count: 33
• Complexity: 787

Purity/Quality:

98%Min ^*data from raw suppliers

2',3'-Di-O-benzoyluridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OC2C(OC(C2OC(=O)C3=CC=CC=C3)N4C=CC(=O)NC4=O)CO

Technology Process of 2,3-DI-O-Benzoyluridine

There total 11 articles about 2,3-DI-O-Benzoyluridine 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: 81.0%

tribenzoyl uridine (1748-04-5) → 2',3'-di-O-benzoyluridine (50408-20-3)

Guidance literature:

With methanol; di(tert-butyl)chlorotinhydroxide dimer; at 66 ℃; for 48h;

DOI:10.1021/jo702249j

Reference yield:

5'-O-dimethoxytrityl-2',3'-O-dibenzoyluridine (78462-56-3) → 2',3'-di-O-benzoyluridine (50408-20-3)

Guidance literature:

With trichloroacetic acid; In chloroform; at -20 ℃; for 0.25h; Yield given;

Reference yield:

benzoyl chloride (98-88-4) → 2',3'-di-O-benzoyluridine (50408-20-3)

Guidance literature:

Multi-step reaction with 2 steps

2: CCl₃COOH / CHCl₃ / 0.25 h / -20 °C

With trichloroacetic acid; In chloroform;

upstream raw materials:

benzoyl chloride

5'-dimethoxytrityluridine

uridine

mono-4-methoxytrityl chloride

Downstream raw materials:

2',3'-O-dibenzoyluridin-5'-yl (4-chlorophenyl β-cyanoethyl phosphate)

C₃₀H₂₃N₂O₁₁P

C₃₀H₂₆N₂O₁₀S

C₄₅H₄₆ClN₂O₂₀P

Refernces

• 1、 Beigelman, Leon N.,Mikhailov, Sergey N.. "Transient protection in nucleoside synthesis using trityl groups: is it necessary to block hydroxyl groups?". . p. 324 - 329. Retrieved 2007/10/02.
• 2、 Lekschas, Joerg,Cech, Dieter,Rosenthal, Andre. "Geschuetzte Ribonucleoside zur chemischen Synthese von RNA-Sequenzen". . p. 329 - 330. Retrieved 2007/10/02.