110522-97-9

Basic information

• Product Name: 5-phenylthiouridine
• Synonyms: 5-phenylthiouridine
• CAS NO: 110522-97-9
• Molecular Weight: 352.368
• Mol File: 110522-97-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-phenylthiouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-phenylthiouridine(110522-97-9)
• EPA Substance Registry System: 5-phenylthiouridine(110522-97-9)

Safety Data

• Hazardous Substances Data: 110522-97-9(Hazardous Substances Data)

Upstream product

• 64898-15-3 2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine 
• 882-33-7 diphenyldisulfane 
• 54503-61-6 2',3'-O-isopropylidene-5-bromouridine 
• 362-43-6 2',3'-O-isopropylideneuridine 
• 116431-58-4 1-((3aR,4R,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-5-phenylsulfanyl-1H-pyrimidine-2,4-dione 
• 110522-91-3 1-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-phenylsulfanyl-1H-pyrimidine-2,4-dione 
• 957-75-5 5-bromouridine 

Relevant articles and documents

Synthesis of 5-arylthiouridines via electrophilic substitution of 5- bromouridines with diaryl disulfides

Novel synthetic method of 5-arylthiouridine derivatives is described. Treatment of 5-bromo-2',3'-O-isopropylideneuridine (1a) with diaryl disulfides in the presence of sodium hydride at ambient temperature gave the 5-arylthiouridines (2) in moderate yields. The present method is devised by virtue of a combination of efficient participation of the 5'-hydroxy group onto the uracil ring and the electrophilic nature of diaryl disulfide, which was applied to the synthesis of 5-arylthio-1-β-D-arabinofuranosyluracils (8).

A SIMPLE AND GENERAL ENTRY TO 5-SUBSTITUTED URUDINES BASED ON THE REGIOSELECTIVE LITHIATHION CONTROLLED BY A PROTECTING GROUP IN THE SUGAR MOIETY

Lithiathion of 2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine with sec-BuLi/TMEDA occurs at the C-5 position with a high regioselectivity and subsequent reactions of the resulting C-5 lithiated species with a variety of electrophiles provides a general entry to 5-substituted uridines.