2,3-AZIRIDINO-2,3-DIDEOXY-D-RIBONO-GAMMA-LACTONE 5-PHOSPHONATE - STEREOCONTROLLED SYNTHESIS FROM D-LYXOSE AND UNUSUAL AZIRIDINE RING-OPENING

The synthesis of hinyl)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (2 3), a new member of the 2,3-aziridino gamma-lactone family of compound s, was achieved in 15 steps from D-lyxose. Like all aziridino gamma-la ctones known so far, 23 reacted with a soft nucleophile (ethanethiol) to give exclusively the product of aziridine ring opening at C-2 (24). On the other hand, hard nucleophiles (alcohols) did not react directl y with the aziridine ring of 23 but appeared to promote intramolecular attack of the aziridine ring at C-3 by the C-5 phosphonate group, res ulting, after hydrolytic workup, in formation of the 2-amino-3-hydroxy -D-ribono-1,4-lactone derivatives 25 and 26, instead of the expected 2 -amino-3-alkoxy-D-xylono-1,4-lactone derivatives.