Pyrrolopyrimidine nucleosides. 18, Synthesis and chemotherapeutic activity of 4-amino-7-(3-deoxy-.beta.-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide (3'-deoxysangivamycin) and 4-amino-7-(2-deoxy-.beta.-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carboxamide (2'-deoxysangivamycin)

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Abstract
A multistep synthesis, using the nucleoside antibiotic toyocamycin as the starting material, has furnished 6,2''-S-cyclosangivamycin (6). Desulfurization of 6 with Raney nickel gave 2''-deoxysangivamycin. Treatment of sangivamycin (1c) with sodium iodide and .alpha.-acetoxyisobutyryl chloride gave 4-amino-7-[2-O-acetyl-3-deoxy-3-iodo-5-O-(2,5,5-trimethyl-4-oxo-1,3-dioxolan-2-yl)-.beta.-D-xylofuranosyl]-pyrrolo[2,3-d]pyrimidine-5-carboxamide (8a). Dehalogenation of 8a with 10% palladium on charcoal was followed by a removal of the blocking groups with ammonium hydroxide to give 3''-deoxysangivamycin in 49% overall yield. The reaction of 1c with diphenyl disulfide and tributylphosphine gave 5''-(phenylthio)-5''-deoxysangivamycin (10). Treatment of 10 with Raney nickel affored 5''-deoxysangivamycin. Antitumor evaluation showed that 3''-deoxysangivamycin had significant activity against the murine leukemia L1210 both in vivo and in vitro, although it was less potent on a molar basis than the parent compound sangivamycin. The 2''- and 5''-deoxysangivamycins did not show significant antitumor activity.