A general route to D- and L-six-membered nucleoside analogues.
A simple synthetic route for novel L-(as well as D-) six-membered nucleosides is described. Particularly, we have provided a general approach to the synthesis of azasugar-based nucleosides, which preparation has been easily achieved starting from the coupling of our three carbon homologating agent 1 with the well known Garner aldehyde 4. Further suitable and stereocontrolled functionalizations of the intermediate 9 will provide, after the base insertion, a wide class of six membered modified azanucleosides to be tested as NRTIs.
Guaragna
Annalisa
A
Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, Napoli, Italy. guaragna@unina.it
D'Alonzo
Daniele
D
De Nisco
Mauro
M
Pedatella
Silvana
S
Palumbo
Giovanni
G
D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry; D001372:Aza Compounds / Q000138:chemical synthesis / Q000737:chemistry; D015195:Drug Design; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000998:Antiviral Agents; D001372:Aza Compounds; D009705:Nucleosides