14985-34-3

Usage

InChI:InChI=1/C16H18N2O6/c19-9-11-13(21)14(22)15(24-11)17-7-6-12(20)18(16(17)23)8-10-4-2-1-3-5-10/h1-7,11,13-15,19,21-22H,8-9H2/t11-,13-,14-,15-/m1/s1

Upstream product

• 100-39-0 benzyl bromide 
• 58-96-8 uridine 
• 100-44-7 benzyl chloride 
• 32464-90-7 N³-benzyl-2',3'-O-isopropylideneuridine 
• 87418-77-7 5'-O-(tert-butyldimethylsilyl)uridine 
• 820212-28-0 3-benzyl-1-[3,4-bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 820212-17-7 N³,2',3'-tribenzyluridine 

Relevant academic research and scientific papers

Structure-Activity Relationship of Purine and Pyrimidine Nucleotides as Ecto-5′-Nucleotidase (CD73) Inhibitors

Cluster of differentiation 73 (CD73) converts adenosine 5′-monophosphate to immunosuppressive adenosine, and its inhibition was proposed as a new strategy for cancer treatment. We synthesized 5′-O-[(phosphonomethyl)phosphonic acid] derivatives of purine and pyrimidine nucleosides, which represent nucleoside diphosphate analogues, and compared their CD73 inhibitory potencies. In the adenine series, most ribose modifications and 1-deaza and 3-deaza were detrimental, but 7-deaza was tolerated. Uracil substitution with N3-methyl, but not larger groups, or 2-thio, was tolerated. 1,2-Diphosphono-ethyl modifications were not tolerated. N4-(Aryl)alkyloxy-cytosine derivatives, especially with bulky benzyloxy substituents, showed increased potency. Among the most potent inhibitors were the 5′-O-[(phosphonomethyl)phosphonic acid] derivatives of 5-fluorouridine (4l), N4-benzoyl-cytidine (7f), N4-[O-(4-benzyloxy)]-cytidine (9h), and N4-[O-(4-naphth-2-ylmethyloxy)]-cytidine (9e) (Ki values 5-10 nM at human CD73). Selected compounds tested at the two uridine diphosphate-activated P2Y receptor subtypes showed high CD73 selectivity, especially those with large nucleobase substituents. These nucleotide analogues are among the most potent CD73 inhibitors reported and may be considered for development as parenteral drugs.

Simultaneous removal of benzyl and benzyloxycarbonyl protective groups in 5′-O-(2-deoxy-α-D-glucopyranosyl)uridine by catalytic transfer hydrogenolysis

Synthesis of N3,2′,3′-O-tris-(benzyloxycarbonyl)uridine and its use in the synthesis of 5′-O-(2-deoxy-α-d-glucopyranosyl)uridine is described. Simultaneous removal of benzyl and benzyloxycarbonyl groups was accomplished by catalytic transfer hydrogenolysis in the presence of Pearlman′s catalyst without competing side reactions. Copyright Taylor & Francis Group, LLC.

Facile deprotection of O-Cbz-protected nucleosides by hydrogenolysis: An alternative to O-benzyl ether-protected nucleosides

(Chemical Equation Presented) Because of side-reactions encountered during hydrogenolysis, benzyl ethers are usually not an effective protecting group for nucleosides. Benzyloxycarbamates provide an alternative to traditional benzyl ethers for protection of nucleoside hydroxyl groups, as they are much more labile to hydrogenolysis. Deprotection conditions using transfer hydrogenolysis are described that avoid the reduction of the pyrimidine nucleobase during deblocking of O-Cbz-protected nucleosides. Additionally, an experiment is described that suggests the nucleobase component of a nucleoside is responsible for the sluggish hydrogenolysis of nucleosides.

N-Substituted Oxopyrimidines and Nucleosides: Structure-Activity Relationship for Hypnotic Activity as Central Nervous System Depressant

N3-Benzyluridine (3-(phenylmethyl)-1-β-D-ribofuranosyluracil) (1f) and its related compounds were synthesized and evaluated for hypnotic activity as central depressants.The primary structural modification has been carried out at the N3/su

Selective 2'-O-Methylation of Pyrimidine-Ribonucleosides by Trimethylsulfonium Hydroxide in the Presence of Mg2+ and Ca2+ Ions

Reactions of various ribonucleosides with trimethylsulfonium hydroxide were investigated in the presence of Mg2+ and Ca2+ ions.The 2'-OH groups of pyrimidine-ribonucleosides were methylated selectively.