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8427952 
Journal Article 
Synthesis of 2′-deoxy-5-fluoro-5′-O-1″,3″,2″-oxazaphosphacyclohexa-2″-yluridine 2″-oxide and related compounds 
Hunston, RN; Jehangir, M; Jones, AS; Walker, RT 
1980 
1 
Tetrahedron
ISSN: 0040-4020 
36 
16 
2337-2340 
English 
2′,3′-O-Isopropylidene-5′-O-1″,3″,2″-oxazaphosphacyclohex-2″-yl-uridine 2″-oxide has been obtained by the action of phosphoryl chloride and N-methylmorpholine, followed by 3-aminopropan-1-ol, on 2',3'-O-isopropy-lidineuridine. A similar reaction carried out on 3'-O-acetylthymidine, followed by removal of the acetyl group gave 5′-O-1″,3″,2″-oxazaphospha-2″-yl-thymidine 2″-oxide. Both of these compounds were obtained more conveniently by treatment of 2',3'-O-isopropylideneuridine and thymidine respectively with 2-chloro-1,3,2-oxazaphosphacyclo-hexane 2-oxide in pyridine. Similar treatment of 2′-deoxy-5-fluorouridine gave 2′-deoxy-5-fluoro-5′-O-1″,3″,2″-oxazaphosphacyclohex-2″-yluridine 2″-oxide. The latter compound was tested for activity against S 180 Crocker sarcoma and L 1210 mouse leukaemia. Only a marginal activity against the S 180 sarcoma was detected. However inactivity of the compound in inducing leukopenia indicated that it might be of low toxicity and that further testing of the compound would be justified. © 1980.