Synthesis of 9-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)adenine Bearing a Slectively Removable Protecting Group

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概要

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• A facile and practicam method to infroduce fluorine at the up-side of the 2'-carbon of nucleosides is described. 6-Chloropurine riboside 3 was converted to the 3'-O-benzoate 4a via a stannylene complex, then converted to the 3'-O-benzoyl-5'-O-tritylriboside 5a. In the presence of pyridine, migration of the 3'-benzoyl groups of 4a and 5a to 2'-OH was rather slow. Hence, 5a was reacted with diethylaminosulfur trifluoride (DAST) in CH_2Cl_2 in the presence of pyridine to give the 2'-deoxy-2'-fluoroarabinoside 6 in good yield. The 3'-O-benzoyl-5'-O-trityl protecting system was easy to deprotect selectively. Thus, treatment of 6 with ammonia in MeOH gave the 5'-O-trityl compound 7,which was subjected to esterificaiton with phenyl chlorothionoformate, radical deoxygenation with tris(trimethylsilyl)silane and acid treatment to afford 9-(2,3-dideoxy-2-fluoro-β-D-threo-pento-furanosyl)adenine(FddA) 2. In addition, acid treatment of 7 gave 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine (FdaraA) 1.

• 1999-07-15

著者

• Maruyama Tokumi

  Faculty Of Pharmaceutical Sciences At Kagawa Campus Tokushima Bunri University

• Izawa K

  Amino Science Laboratories Ajinomoto Co. Inc.

• Kozai Shigetada

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

• Kozai Shigetada

  Faculty Of Pharmaceutical Science Tokushima Bunri University

• Takamatsu S

  Amino Science Laboratories Ajinomoto Co. Inc.

• TAKAMATSU Satoshi

  Amino Science Laboratories, Ajinomoto Co., Inc.,

• SATOH Yoshiko

  Faculty of Pharmaceutical Sciences, Tokushima Bunri University

• IZAWA Kunisuke

  Amino Science Laboratories, Ajinomoto Co., Inc.,

• Satoh Yoshiko

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

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• Synthesis of 9-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)adenine Bearing a Slectively Removable Protecting Group
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