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Synthesis 1990; 1990(5): 411-415
DOI: 10.1055/s-1990-26890
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Synthesis of 2′,3′-Didehydro-2′,3′-dideoxyformycin A, 2prime;,3′-Dideoxyformycin A and 2′,3′-Dideoxytubercidin

Pawel Serafinowski*
  • *Drug Development Section, Cancer Research Campaign Laboratories, Institute of Cancer Research, Cotswold Road, Sutton, Surrey, SM2 5NG, England
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Publication History

Publication Date:
17 September 2002 (online)

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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]-1H-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 deoxygenation of their respective 3′-deoxy counterparts 10 and 2, respectively.

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