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 Production Routes of Lodenosine
  • Production Routes of Lodenosine
  • Lodenosine (CAS NO.: 110143-10-7), with its systematic name of 9H-Purin-6-amine, 9-(2,3-dideoxy-2-fluoro-beta-D-threo-pentofuranosyl)-, could be produced through many synthetic methods.

    Following are some of the synthesis routes:

    Route one:
    The selective tritylation of cordycepin (3-deoxyadenosine) (I) with trityl chloride in pyridine produces the 5-O-trityl derivative (II), which is then fluorinated with diethylamido sulfur trifluoride in refluxing dichloromethane and deprotected with hot 80% acetic acid.

    Production Route of Lodenosine

    Route two:

    Production Route of Lodenosine

    Firstly, 1,3,5-Tri-O-benzoyl-2-deoxy-2-fluoro-alpha-D-arabinofuranose (XI) reacts with HBr in acetic acid to produce the bromosugar (XXII), which is condensed with 6-chloropurine (V) as before, affording 6-chloro-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)purine (XXIII). Next, this compound is treated with ammonia in methanol as before to afford intermediate 9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)adenine (VII).


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