2'-chloro-2', 3'-dideoxy-3'-fluoro-D-ribonucleosides: synthesis, stereospecificity, some chemical transformations, and conformational analysis

IA Mikhailopulo, TI Pricota, GG Sivets…

Index: Mikhailopulo, Igor A; Pricota, Tamara I; Sivets, Grigorii G; Altona, Cornelis The Journal of organic chemistry, 2003 ,  vol. 68,  # 15  p. 5897 - 5908

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Citation Number: 47

Abstract

The synthesis of methyl 5-O-benzoyl-2-chloro-2, 3-dideoxy-3-fluoro-β-d-ribofuranoside (5) and its use as a glycosylating agent for persilylated thymine, N 6-benzoyladenine, and N 4- benzoylcytosine are described (Scheme 1). The 2'-chloro-2', 3'-dideoxy-3'-fluoro-d- ribonucleosides 10-12 synthesized were transformed to 2', 3'-dideoxy-3'-fluoro-α-and-β-d- erythro-pentofuranoside nucleosides of thymine (13a, b), adenine (14a, b), and cytidine ( ...