Synthese monofluorierter cyclopropanoider Nucleosidanaloga Synthesis of Monofluorinated Cyclopropanoic Nucleoside Analogues

Synthese monofluorierter cyclopropanoider Nucleosidanaloga Synthesis of Monofluorinated Cyclopropanoid Nucleoside Analogues

Infektionskrankheiten stellen trotz der großen Erfolge in der Bekämpfung auch heute noch eine ernste gesundheitliche Bedrohung für die Menschen dar. Weltweit fallen ihnen ca. 17 Millionen Menschen jährlich zum Opfer. Impfmüdigkeit in der Bevölkerung, Ferntourismus und zunehmende Resistenz der Erreger gegen Antibiotika begünstigen die Verbreitung bekannter Infektionserkrankungen. Neue Erreger, w...

Chemical Synthesis of Nucleoside Analogues Chemical Synthesis of Nucleoside Analogues

An efficient solid phase synthesis of 5'-phosphodiester and phosphoramidate monoester nucleoside analogues.

An easy and efficient strategy to obtain libraries of 5'-phosphodiester and 5'-phosphoramidate monoester nucleoside analogues in a highly pure form has been developed, starting from a new nucleoside based solid support. The nucleoside scaffold has been anchored through a 5'-phosphodiester linkage to Tentagel HL resin, functionalized with a 3-chloro-4-hydroxyphenylacetic linker. The solid phase ...

Synthesis of Novel 2′(β)-Methyl-5′-deoxyapiose Nucleoside Phosphonic Acid Analogues as Antiviral Agents

Novel 2'(β)-methyl-5'-deoxyapiose purine phosphonic acid analogues were designed and synthesized from 2-propanone1,3-diacetate. Condensation successfully proceeded from a glycosyl donor 9 under Vorbrüggen conditions. Condensation of aldehyde 14 with Wittig reagent [(diethoxyphosphinyl)methylidene] triphenylphosphorane gave the desired nucleoside phosphonate analogues 15. Ammonolysis and hydroly...

Photochemical synthesis of nucleoside analogues from cyclobutanones: bicyclic and isonucleosides.

The preparation of two nucleoside analogues are reported. Both syntheses involve a key photochemical ring-expansion of cyclobutanones to an oxacarbene and its subsequent scavenging by 6-chloropurine. The synthesis of a bicyclic (locked) purine starts from a oxabicycloheptanone with a hydroxymethyl pendant. The preparation of an isonucleoside uses a cyclobutanone with an alpha-substituted 6-chlo...