Synthesis of 3'-azido- and 3'-amino-3'-deoxyadenosine in both enantiomeric forms

Article abstract of DOI:10.1016/S0040-4020(98)00819-9

Aminosugar nucleosides are important bioactive molecules of which puromycin, a derivative of 3'-amino-3'-deoxyadenosine, is one of the most important examples. Some azidosugar nucleosides, the synthetic precursors of the corresponding aminosugar compounds, are known to be active against HIV reverse transcriptase. We are interested in comparing the bioactivity of D- and L-enantiomers of such nucleosides. Here, the synthesis of both D- and L- enantiomers of 3'-azido- and 3'-amino-3'-deoxyadeonsine, respectively, is described. It begins with the introduction of the nitrogen functionality through a substitution reaction with inversion at C-3 of a D- or L-xylose derivative, respectively. The azidosugar is converted into an appropriate glycosyl donor which is the submitted to a glycosidation reaction according to Vorbruggen. Deprotection affords 3'azido-3'-deoxy-D/L-adenosine, our potentially antiviral target compounds, and reduction of the azido substituent leads to the aminosugar target molecules.