Nucleotides. V. Purine Ribonucleoside 2',3'-Cyclic Carbonates. Preparation and Use for the Synthesis of 5'-Monosubstituted Nucleosides^*

Abstract

Acid-catalyzed ester exchange reactions between diphenyl carbonate and inosine, adenosine, and 5 '-O-tritylinosine have given good yields of the respective nucleoside 2',3'-cyclic carbonates. Prior pro-

Thienyl-Substituted Nucleosides and Their Triphosphates

“…D-ribofuranosyl)-S-(2"-thienyl)-uracil (2) and 1-(2',3',S'-tri-O-benzoyl-f3-D-ribofuranosyl)-S-(2"-thienyl)cytosine (8) were 83 and 76%, respectively. Removal of the benzoyl groups with sodium methoxide resulted in the corresponding 1-([3-D-ribofuranosyl)-S-(2"-thienyl)uracil (3) in 73% yield and the 1-([3-D-ribofuranosyl)-S-(2"-thienyl)cytosine (9) of the unprotected ribo-U derivative (3) with diphenyl carbonate (Hampton and Nichol, 1966) …”

Uridine Binding Motifs of Human Concentrative Nucleoside Transporters 1 and 3 Produced inSaccharomyces cerevisiae

“…Chemical, Inc. (Orange, CA). 1-(␤-D-Arabinofuranosyl)uracil (Codington et al, 1960;Hampton and Nichol, 1966), 2Ј-azido-2Ј-deoxyuridine (Verheyden et al, 1971), 2Ј-O-methyluridine (Robins et al, 1974), 1-(␤-D-xylofuranosyl)uracil (Yung and Fox, 1961), 3Ј-deoxyuridine (Rhie and Pfleiderer, 1994), 3Ј-azido-3Ј-deoxyuridine (Matray and Gryaznov, 1999), 5Ј-deoxyuridine (Wang et al, 1977), 5Ј-chloro-5Ј-deoxyuridine (Robins et al, 1991), 5Ј-azido-5Ј-deoxyuridine (Horwitz et al, 1962), and 5Ј-O-methyluridine (Hovinen, 1997) were prepared as described in the references noted. 3Ј,5Ј-Dideoxyuri- The transport of 1 M ͓ 3 H͔Urd into yeast (fui1::TRP) expressing either pYPhCNT1 or pYPhCNT3 was measured over 30 or 10 min, respectively, in the presence of graded concentrations of Urd or Urd analogs.…”

A General Synthesis of 8,2′-Thioanhydropurine Nucleosides

“…Further it has been found that there is no need to block either the 5'-hydroxyl or amine groups on the base ring in forming 2',3'-carbonates of purine nucleosides (16,35). This suggested the possibility of introducing a good leaving group (CO,) on the 2'-position of any 8-halopurine nucleoside in a single step.…”