A practical synthesis of nucleoside 5′-diphosphates from nucleoside 5′-H-phosphonate monoesters

Abstract

S6 -S81 H, 13 C and 31 P NMR spectra of adenosine 5′-diphosphate (6a), bis TEAH + salt S9 -S11 1 H, 13 C and 31 P NMR spectra of guanosine 5′-diphosphate (6b), bis TEAH + salt S12 -S14 1 H, 13 C and 31 P NMR spectra of cytidine 5′-diphosphate (6c), bis TEAH + salt S15 -S17 1 H, 13 C and 31 P NMR spectra of uridine 5′-diphosphate (6d), bis TEAH + salt S18 -S20 1 H, 13 C and 31 P NMR spectra of deoxyadenosine 5′-diphosphate (6e), bis TEAH + salt S21 -S23 1 H, 13 C and 31 P NMR spectra of deoxyguanosine 5′-diphosphate (6f), bis TEAH + salt S24 -S26 1 H, 13 C and 31 P NMR spectra of deoxycytidine 5′-diphosphate (6g), bis TEAH + salt S27 -S29 1 H, 13 C and 31 P NMR spectra of thymidine 5′-diphosphate (6h), bis TEAH + salt S30 -S32 1 H, 13 C and 31 P NMR spectra of 3′-azido-3′-deoxythymidine 5′-diphosphate (6i), bis TEAH + salt S33 -S35 1 H, 13 C and 31 P NMR spectra of 2′,3′-didehydro-2′,3′-dideoxythymidine 5′diphosphate (6j), bis TEAH + salt S36 -S38 1 H, 13 C and 31 P NMR spectra of 3′-O-benzoyl-5-fluoro-2′-deoxyuridine 5′diphosphate (6k), bis TEAH + salt S39 -S41 1 H, 13 C and 31 P NMR spectra of bis(3′-azido-3′-deoxythymidine) 5′,5′′triphosphate (9), tris TEAH + salt

The First 5′-Phosphorylated 1,2,3-Triazolyl Nucleoside Analogues with Uracil and Quinazoline-2,4-Dione Moieties: A Synthesis and Antiviral Evaluation

“…Unfortunately, the isolation of 5′-phosphates 25a , b and 26a , b by chromatography methods turned out to be difficult due to the impurity of trimethylammonium salts of phosphoric acid, which could not be separated either by flash chromatography with gradient elution or chromatography on ion exchange resins. Having failed in the isolation of individual 5′-phosphates 25a , b and 26a , b synthesized by the known methodology [ 56 , 57 ], we used another approach based on the oxidation of 5′-trimethylsilyl- H -phosphonate monoesters with elemental iodine [ 58 ]. The 2′,3- O -isopropylidene-protected nucleoside H -phosphonate monoesters 21a , b and 22a , b were first converted into the trimethylsilyl H -phosphonate diesters 27a , b and 28a , b (using 3 mol.…”