113548-93-9

Basic information

• Product Name: 2',3'-bis(benzyloxy)-5-fluorouridine
• Synonyms: 2',3'-bis(benzyloxy)-5-fluorouridine
• CAS NO: 113548-93-9
• Molecular Weight: 442.444
• Mol File: 113548-93-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2',3'-bis(benzyloxy)-5-fluorouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-bis(benzyloxy)-5-fluorouridine(113548-93-9)
• EPA Substance Registry System: 2',3'-bis(benzyloxy)-5-fluorouridine(113548-93-9)

Safety Data

• Hazardous Substances Data: 113548-93-9(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 3871-66-7 5-fluoro-1-(5′-O-trityl-β-D-ribofuranosyl)uracil 

Downstream Products

• 113548-96-2 5'-deoxy-4',5-difluoro-2',3'-bis(benzyloxy)uridine 
• 113548-95-1 1-(5-deoxy-2,3-bis(benzyloxy)-β-D-erythro-pent-4-enofuranosyl)-5-fluorouracil 
• 113548-97-3 5'-deoxy-4',5-difluorouridine 
• 113548-94-0 5'-O-mesyl-2',3'-bis(benzyloxy)-5-fluorouridine 

Relevant articles and documents

Synthesis and interaction with uridine phosphorylase of 5'-deoxy-4',5-difluorouridine, a new prodrug of 5-fluorouracil

5'-Deoxy-4',5-difluorouridine (4'-F-5'-dFUrd) (10) has been synthesized on the basis of the rationale that the labilization of the glycosidic linkage caused by the 4'-fluoro substituent might allow this compound to be a better prodrug form of the anticancer drug 5-fluorouracil (FUra) than is the widely studied fluoropyrimidine 5'-deoxy-5-fluorouridine (5'-dFUrd). The rate of solvolytic hydrolysis of the glycosidic linkage of 4'-F-5'-dFUrd at pH 1 was about 500-fold faster than that of 5'-dFUrd. Since uridine phosphorylase is thought to be the enzyme that causes degradation of 5'-dFUrd in vivo to generate FUra, we compared the substrate interactions of 5'-dFUrd and 4'-F-5'-dUrd with this enzyme. The V(max) for hydrolysis of 4'-F-5'-dFUrd to FUra by uridine phosphorylase was about 5-fold greater than that of 5'-dFUrd, whereas the K(m) value of 4'-F-5'-dFUrd was 10-fold lower. The combination of these two factors results in 4'-F-5'-dRUrd having a 50-fold higher value of V/K than does 5'-dFUrd. Against L1210 cells in culture, the IC50 value for growth inhibition by 4'-F-5'-dFUrd was 3 x 10-7 compared to 3 x 10-6 for 5'-dFUrd.