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Synthesis 1990; 1990(9): 757-760
DOI: 10.1055/s-1990-27006
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Synthesis of 2′,3′-Dideoxy-3-deazaadenosine and Some of its Analogues

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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Glycosylation of 4-chloro-1H-imidazo[4,5-c]pyridine (1) with 2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythropentofuranosyl chloride (2) and subsequent deprotection of the resulting products 3a and 3b yielded 4-chloro-1-(2-deoxy-β-D-erythropentofuranosyl)- 1H-imidazo[4,5-c]pyridine (4a) and 4-chloro-3-(2-deoxy- β-D-erythropentofuranosyl)- 1H-imidazo[4,5-c]pyridine (4b), respectively. Deoxygenation of 4a gave 4-chloro-1-(2,3-dideoxy- β-D-glyceropentofuranosyl)- 1H-imidazo[4,5-c]pyridine (8). Finally, amination of 4a, 4b and 8 afforded 2′-deoxy-3- deazaadenosine (9a), 4-amino-3-(2-deoxy-β-D-erythropentofuranosyl)- 1H-imidazo-[4,5-c]pyridine (9b) and 2′,3′-dideoxy-3 -deazaadenosine (9c), respectively.