Synthesis of 2',3'-didehydro-2',3'-didoxyformycin A, 2',3'-Dideoxyformycin A and 2',3'-Dideoxytubercidin

Article abstract of DOI:10.1055/s-1990-26890

2',3'-Didehydro-2',3'-dideoxyformycin A (7) was prepared by reaction of the 7-amino-3-[5-O-(2-acetoxyisobutyryl)-3-bromo-3-deoxy-2-O- phenoxy(thiocarbonyl)-β-D-xylofuranosyl]-1 H-pyrazolo [4,3-d]-pyrimidine (5) or 7-amino-3-[5-O-(2-acetoxyisobutyryl)-2- bromo-2-deoxy-3-O-phenoxy(thiocarbonyl)-β-D-arabinofuranosyl]-1 H-pyrazolo[4,3-d]pyrimidine (9) with tributyltin hydride and subsequent deprotection of the resulting 5'-O-(2-acetoxyisobutyryl)-2',3'-didehydro-2',3'-dideoxyformycin A (6). 2',3'-Dideoxyformycin A (13) and 2',3'-dideoxytubercidin (16) were synthesized via deoxygeneration of their respective 3'-deoxy counterparts 10 and 2, respectively.