Studies directed toward the synthesis of 2'-deoxy-2'-substituted arabino nucleosides.

K. W. Pankiewicz; B. Nawrot; E. Sochacka; K. A. Watanabe

Studies directed toward the synthesis of 2'-deoxy-2'-substituted arabino nucleosides.

K. W. Pankiewicz, B. Nawrot, E. Sochacka, K. A. Watanabe

Center for Drug Design

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4 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	257-260
Number of pages	4
Journal	Nucleic acids symposium series
Issue number	18
State	Published - 1987

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abstract = "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.",

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AU - Pankiewicz, K. W.

AU - Nawrot, B.

AU - Sochacka, E.

AU - Watanabe, K. A.

PY - 1987

Y1 - 1987

N2 - 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.

AB - 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.

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Studies directed toward the synthesis of 2'-deoxy-2'-substituted arabino nucleosides.

Abstract

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