Studies of nucleosides and nucleotides. LXXXII. Cyclonucleosides. (39). Synthesis and properties of 2'-halogeno-2'-deoxyadenosines.

1 January 1978

journal article
Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN

Vol. 26 (8) , 2449-2453
https://doi.org/10.1248/cpb.26.2449

Abstract

9-(2'-O-Methanesulfonyl- or trifluoromethanesulfonyl-3', 5'-di-O-tetrahydropyranyl-β-D-arabinofuranosyl) adenine (Ia, b) were reacted with lithium chloride or tetrabutylammonium halide to yield 2'-halogeno-2'-deoxy compounds (IIa-d). These halogeno compounds were deprotected with 80% acetic acid to give 2'-chloro-, 2'-bromo-, 2'-fluoro and 2'-iodo-2'-deoxyadenosine (IVa-d) in overall yields of 12-25% from the compound I. Ultraviolet absorption properties, 1H and 13C-nuclear magnetic resonance spectral properties were recorded on the compounds IVa-d.

Keywords

^C-NMR

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