Introduction of α-fluorophosphonomethyl ether functionality and its application to the synthesis of fluorinated acyclic phosphonate nucleosides

✍ Scribed by Wei Chen; Michael T. Flavin; Robert Filler; Ze-Qi Xu

• Publisher: Elsevier Science
• Year: 1996
• Tongue: French
• Weight: 201 KB
• Volume: 37
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02106-5

✦ Synopsis

Introduction of the a-fluorophosphonomethyl ether functionality has been achieved by electro~hilic fluorination of the corresponding phosphonomethyl ether carbanion. Coupling of the synthesized 2-[(diethoxyphosphono)fluoromethoxy]ethanol (

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) with adenine and 6-chloropurine under Mitsunobu conditions afforded novel fluorinated acyclic phosphonate nucleosides lla and lib, respectively.