5975-05-3

Usage

Molecular Weight

284.27 g/mol

Derivative of

Isocytidine (a nucleoside analogue)

Application in Nucleic Acid Research

Used as a starting material for chemical synthesis of modified nucleosides and nucleotides

Medical Applications

Development of antiviral drugs
Development of anticancer drugs

Mechanism of Action

Interferes with the replication of viral and cancerous cells

Role in Studying Structure-Activity Relationships

Valuable tool for investigating the structure-activity relationships of nucleoside analogues

Biological Effects

Studying the biological effects of nucleoside analogues

Upstream product

• 77-76-9 2,2-dimethoxy-propane 
• 489-59-8 2-amino-1-(β-D-ribofuranosyl)pyrimidin-4(1H)-one 
• 14671-65-9 5'-deoxy-5'-iodo-2',3'-O-isopropylideneuridine 
• 58-96-8 uridine 
• 53337-87-4 (3aR,4R,12R,12aR)-2,2,2-triphenyl-4,5,12,12a-tetrahydro-2H,3aH,8H-4,12-epoxy-2λ5-[1,3,2]dioxaphospholo[4,5-e]pyrimido[2,1-b][1,3]-oxazocin-8-one 
• 3868-21-1 2',3'-O-isopropylidene-O²,5'-cyclouridine 

Relevant academic research and scientific papers

Studies on Nucleosides and Nucleotides. VIII. Preparation and Reactions of Triphenylphosphoranediylnucleosides

The reaction of uridine, N4-benzoylcitidine, guanosine, and N6-p-toluoyladenosine with diethyl azodicarboxylate and triphenylphosphine resulted in the formation of the corresponding 2',3'-O-(triphenylphosphoranediyl)cyclonucleosides.On the other hand, adenosine afforded, under similar conditions, 3',5'-O-(triphenylphosphoranediyl)adenosine (19).The difference can be explained in terms of the acidity of base moieties of the nucleosides.The reaction of 2',3'-O-(triphenylphosphoranediyl)-O2,5'-cyclouridine, N4-benzoyl-2',3'-O-(triphenylphosphoranediyl)-O2,5'-cyclocytidine, 2',3'-O-(triphenylphosphoranediyl)-N3,5'-cycloguanosine, or N6-p-toluoyl-2',3'-O-(triphenylphosphoranediyl)-N3,5'-cycloadenosine with nucleophiles and with electrophiles addorded the corresponding nucleoside derivatives with free 2'- and 3'-hydroxyl groups.Thus the 2',3'-O-triphenylphosphoranediyl group serves as a protecting group which is readily removed during work-up of the reaction products. 19 reacted with phenyl isocyanate to give 5'-O-phenylcarbamoyladenosine and N6,5'-O-bis(phenylcarbamoyl)adenosine.The reaction of 19 with diphenylketene also afforded acyladenosines with free 2'- and 3'-hydroxyl groups.These results suggested that 3',5'-O-triphenylphosphoranediyl group activates the 5'-carbon atom of adenosine.