Pyrimidine Nucleosides. VII. Reactions of 2',3',5'-Trimesyloxyuridine¹

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.…”

[d4U]-Spacer-[HI-236] double-drug inhibitors of HIV-1 reverse-transcriptase

“…This methodology could be carried out efficiently on a several-grm-scale with a single clean-up chromatography step at the end and was superior to other methodologies25 such as that using acetyl bromide 26. Thus, mesylation of the hydroxyl groups of uridine, followed by heating the product with sodium benzoate in acetamide furnished the 2′-anhydro nucleoside 8 24b. Subsequent opening using HBr (from AcBr in MeOH) to bromomesylate 9 followed by zinc-mediated elimination furnished the 5′-benzoate of d4U 10 26a as a crystalline solid.…”

“…For synthesis of the left-hand nucleoside partner, advantage was taken of the elegant Bristol-Myers Squibb process for converting 5-methyluridine into d4T23 based on seminal work by Fox involving uridine 24. This methodology could be carried out efficiently on a several-grm-scale with a single clean-up chromatography step at the end and was superior to other methodologies25 such as that using acetyl bromide 26.…”

Locked Nucleic Acids: Synthesis and Characterization of LNA‐T Diol

“…This two‐step one‐pot procedure is fast and smooth compared to the two‐step procedure originally described (Koshkin et al, ,b). The methanesulfonyloxy group is substituted with benzoyl upon reaction of S.9 with sodium benzoate in hot DMF (Codington et al, ), followed by hydrolysis of the benzoate ester using LiOH to give S.11 in 79% yield (four steps) after crystallization from hexanes. Direct basic hydrolysis of the 5′‐ O ‐methanesulfonyl group was unsuccessful (Koshkin et al, ).…”