Studies directed toward the synthesis of 2'-deoxy-2'-substituted arabino nucleosides.
Synthesis of the C-nucleoside, 5-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-1-methyluracil, isosteric to the potent antiviral and anticancer nucleoside, 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-1-methyluracil (2'-fluoro-5-methyl-ara-U or FMAU) was achieved by exploitation of the 4,5'-anhydro-nucleoside. Attempts at application of this ribosyl-to-arabinosyl pyrimidine transformation to 2,5'-anhydrouridine resulted in the formation of 2,2'-anhydro-5-substituted-arabinosyluracil.
Pankiewicz
K W
KW
Sloan-Kettering Institute for Cancer Research, Graduate School of Medical Sciences, Cornell University, New York, NY 10021.
Nawrot
B
B
Sochacka
E
E
Watanabe
K A
KA
D001087:Arabinonucleosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents
D001087:Arabinonucleosides; D007202:Indicators and Reagents