Synthesis of a xylo-Puromycin Analogue

N 6 -Bis-demethylated xylo-puromycin analogue 2 was synthesized over six steps in 56% yield from adenosine 3, involving a Mattocks bromoacetylation, a regio- and stereoselective ribo-epoxide ring opening with sodium azide and an efficient Staudinger-Vilarrasa reaction to couple the amino acid to an azide precursor.