PREPARATION OF THE ENANTIOMERIC FORMS OF 9-(5-DEOXY-ALPHA-THREO-PENT-4-ENOFURANOSYL) ADENINE AND 9-(3,5-DIDEOXY-BETA-D-GLYCERO-PENT-4-ENOFURANOSYL)ADENINE AND INVITRO ANTI-LEUKEMIC SCREENING

The preparation and use of 5-deoxy-5-iodo-l, 2-O-isopropylidene-α-D-xylofuranose and 5-deoxy-5-iodo-l, 2-O-isopropylidene-A-D-arabinofuranose in the synthesis of the L and D forms of 9-(5-deoxy-β-thero-pent-4-enofuranosyl)adenine, respectively, are described. The preparation of 9-(3, 5-dideoxy-β-D-giycero-pent-4-enofuranosyl)adenine (19) was accomplished from either 3, 5-dideoxy-5-iodo-l, 2-O-isopropylidene-α-D-eryffaro-pentofuranose or 3, 5-dideoxy-5-iodo-l, 2-O-isopropylidene-β-L-threo-pentofuranose. In each case, acetolysis was performed to obtain the acetates which were condensed with 6-(benzamidochloromercuri)purine by the titanium tetrachloride method. Treatment with l, 5-diazabicyclo[5.4.0]undec-5-ene and removal of the blocking groups produced the desired nucleosides. Only 19 showed inhibitory activity toward leukemia L1210 in vitro. © 1979, American Chemical Society. All rights reserved.