85267-77-2

Basic information

• Product Name: 3-(3,5-Di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-(2-hydroxyethyl)furano<2,3-d>pyrimidin-2-one
• CAS NO: 85267-77-2
• Molecular Weight: 380.354
• Mol File: 85267-77-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-(3,5-Di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-(2-hydroxyethyl)furano<2,3-d>pyrimidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3,5-Di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-(2-hydroxyethyl)furano<2,3-d>pyrimidin-2-one(85267-77-2)
• EPA Substance Registry System: 3-(3,5-Di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-(2-hydroxyethyl)furano<2,3-d>pyrimidin-2-one(85267-77-2)

Safety Data

• Hazardous Substances Data: 85267-77-2(Hazardous Substances Data)

Upstream product

• 75014-48-1 4-<(triphenylmethyl)oxy>-1-butyne 
• 1956-30-5 3',5'-O-diacetyl-5-iodo-2'-deoxyuridine 

Relevant articles and documents

Nucleic Acid Related Compounds. 39. Efficient Conversion of 5-Iodo to 5-Alkynyl and Derived 5-Substituted Uracil Bases and Nuleosides

Coupling of terminal alkynes with 5-iodo-1-methyl-uracil and 5-iodouracil nucleosides (protected as their p-toluyl esters) proceeded in high yields in the presence of bis(triphenylphosphine)palladium(II) chloride and copper(I)iodide in warm triethylamine.Several of the subsequently deprotected 5-alkynyl-2'-deoxyuridines, including the parent 5-ethynyl-2'-deoxyuridine, had antiviral activity, and their 5'-monophosphates inhibited thymidylate synthetase.Hydrogenation of the 5-alkynyl side chain can be controlled to give (Z)-5-alkenyl- or the saturated 5-alkyl-2'-deoxyuridines.This provides a stereocontrolled route to the known 5-ethyl-and 5-n-hexyl-2'-deoxyuridines as well as (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU).Hydration of the triple bond gave the corresponding uracil-5-alkanone products in favorable cases.