ChemInform Abstract: Nucleoside H‐Phosphonates. Part 18. Synthesis of Unprotected Nucleoside 5′‐H‐Phosphonates and Nucleoside 5′‐H‐Phosphonothioates and Their Conversion into the 5′‐Phosphorothioate and 5′‐Phosphorodithioate Monoesters.

Jankowska, Joanna; Sobkowska, Anna; Cieślak, Jacek; Sobkowski, Michał; Kraszewski, Adam; Stawiński, Jacek; Shugar, David

doi:10.1002/chin.199914261

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“…Nucleoside 5′-H-phosphonates were obtained using method described earlier. 1,2 All synthesized compounds were of purity higher than 98% as judged from 1 H NMR spectroscopy.…”

Section: Methodsmentioning

confidence: 99%

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

Rachwalak

Rozniewska

Gołębiewska

et al. 2020

Synthetic Communications

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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

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“…Nucleoside 5′-H-phosphonates were obtained using method described earlier. 1,2 All synthesized compounds were of purity higher than 98% as judged from 1 H NMR spectroscopy.…”

Section: Methodsmentioning

confidence: 99%

“…13 C NMR (100 MHz, D2O, 25°C): δC (ppm) 8.2, 39.2, 46.6, 64.9, 70.5, 85.4, 85.9, 96.4, 141.8, 156.7, 165.5. 31 P NMR (162 MHz, D2O, 25°C): δP (ppm) -10.35 (d, 2 JP,P = 20.5 Hz, Pβ), -11.28 (d, 2 JP,P = 20. 4 Hz,Pα).…”

Section: Spectroscopic Data Of Compounds 6a-6k Andmentioning

confidence: 99%