Synthesis of 2,3-aziridino-2,3-dideoxy-D-lyxono-γ-lactone 5-phosphonate from D-ribose, a new member of the 2,3-aziridino-γ-lactone family of synthons
A formal synthesis of the novel (1S,4S,5R)-N-(benzyloxycarbonyl(-4-diethoxyphosphinyl)methyl-3-oxa-6 -azabicyclo[3.1.0]hexan-2-one 4 from D-ribose is presented. A key step involves the use of the 2,3-sulfate 12 for introduction of the C-3 azide functionality prior to aziridine ring formation.
Dauban, Philippe,Hofmann, Bernhard,Dodd, Robert H.