Nucleosides. XXXIX. 2'-Deoxy-2'-fluorocytidine, 1-.beta.-D-arabinofuranosyl-2-amino-1,4(2H)-4-iminopyrimidine, and related derivatives

Nucleosides. XLIX. Nuclear magnetic resonance studies of 2′-and 3′-halogeno nucleosides. The conformations of 2′-deoxy-2′-fluorouridine and 3′-deoxy-3′-fluoro-β-D-arabinofuranosyluracil

“…spectroscopy, the effect of halogeno substituents on the 5-membered furanose ring. Therefore, 2'-deoxy-2'-iodo-uridine (I), the diacetates of the 2'-bromo, 2'-iodo, and 2'-deoxy nucleosides (2), and the 3'-halogeno nucleosides, 3(F, Cl, I),were prepared. The complete series studied is listed in Fig.…”

Chemistry at the 2′ Position of Constituent Nucleotides Controls Degradation Pathways of Highly Modified Oligonucleotide Molecules

“…Similarly, the mass determined in this chromatographic injection for the antisense strand at 6759.8 differs from its calculated average value of 6761.0 by 1.2 amu. Peaks 1, 2, and 3 in the UV chromatogram have an averaged mass of 6838.6, differing from the observed sense strand mass by 20.4 amu, which likely corresponds to impurities in which a proton and a fluorine atom have been removed from one of the 8 available 2 0 deoxy-2 0 -fluororibonucleotides in the sense strand to form a 2,2 0 -O-anhydroribonucleotide (Doerr and Fox, 1967). Impurities with a nominal mass difference of 20 amu from the parent strand were also detected in the control sample, though at much lower levels.…”

Recent advances in the synthesis of fluorinated nucleosides

“…3). 52 In addition, 2 0 afluoro-2 0 -deoxyadenosine 15 and 2 0 a-fluoro-2 0 -deoxyguanosine 16 were also synthesized by the Ranganathan group 53 and Kawasaki's group, 54 respectively. Both groups introduced the fluorine atoms into the 2 0 -position via nucleophilic substitution of the corresponding triflate with TBAF.…”