77875-88-8

Basic information

• Product Name: 5-Hexynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine
• Synonyms: 5-Hexynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine
• CAS NO: 77875-88-8
• Molecular Weight: 544.604
• Mol File: 77875-88-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5-Hexynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hexynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine(77875-88-8)
• EPA Substance Registry System: 5-Hexynyl-3',5'-di-O-p-toluyl-2'-deoxyuridine(77875-88-8)

Safety Data

• Hazardous Substances Data: 77875-88-8(Hazardous Substances Data)

Upstream product

• 31356-86-2 1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodouracil 
• 693-02-7 hex-1-yne 

Downstream Products

• 57741-93-2 5-(hexyl)-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 

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.