N(3)-benzyluridine

Base Information

• Chemical Name: N(3)-benzyluridine
• CAS No.: 14985-34-3
• Molecular Formula: C16H18 N2 O6
• Molecular Weight: 334.329
• Mol file: 14985-34-3.mol

Synonyms:Uridine,3-benzyl- (8CI); N3-Benzyluridine

Chemical Property of N(3)-benzyluridine

Chemical Property:

• Vapor Pressure: 1E-14mmHg at 25°C
• Boiling Point: 589.1°Cat760mmHg
• PKA: 13.26±0.70(Predicted)
• Flash Point: 310.1°C
• PSA: 113.92000
• Density: 1.525g/cm³
• LogP: -1.33020

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N(3)-benzyluridine

There total 8 articles about N(3)-benzyluridine 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: 100.0%

N3,2',3'-tribenzyluridine (820212-17-7) → 3-<(phenyl)methyl>-1-β-D-ribofuranosyluracil (14985-34-3)

Guidance literature:

With hydrogen; acetic acid; palladium dihydroxide; In ethanol; ethyl acetate; for 12h;

DOI:10.1021/ol048426w

Reference yield: 88.0%

benzyl bromide (100-39-0) + uridine (58-96-8) → 3-<(phenyl)methyl>-1-β-D-ribofuranosyluracil (14985-34-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 3h; Heating;

DOI:10.1246/bcsj.59.2947

Reference yield: 69.0%

uridine (58-96-8) → 3-<(phenyl)methyl>-1-β-D-ribofuranosyluracil (14985-34-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; acetone; at 55 - 60 ℃; for 72h;

DOI:10.1021/acs.jmedchem.9b00164

upstream raw materials:

benzyl bromide

uridine

N³,2',3'-tribenzyluridine

3-benzyl-1-[3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Refernces

• 1、 Junker, Anna,Renn, Christian,Dobelmann, Clemens,Namasivayam, Vigneshwaran,Jain, Shanu,Losenkova, Karolina,Irjala, Heikki,Duca, Sierra,Balasubramanian, Ramachandran,Chakraborty, Saibal,B?rgel, Frederik,Zimmermann, Herbert,Yegutkin, Gennady G.,Müller, Christa E.,Jacobson, Kenneth A.. "Structure-Activity Relationship of Purine and Pyrimidine Nucleotides as Ecto-5′-Nucleotidase (CD73) Inhibitors". . p. 3677 - 3695. Retrieved 2019.
• 2、 Johnson II, David C.,Widlanski, Theodore S.. "Facile deprotection of O-Cbz-protected nucleosides by hydrogenolysis: An alternative to O-benzyl ether-protected nucleosides". . p. 4643 - 4646. Retrieved 2007/10/03.