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Unformatted text preview: Kelley Krueger Application of Oxidation/Reduction and Coupling Reactions in Synthesis Objective: The article, Synthesis and Conformational Analysis of 1-[2, 4-Dideoxy-4-C- hydroxymethyl-r-L-lyxopyranosyl] thymine, was written to document the stereoselective way to synthesis a pyranose nucleoside with a 1, 4 substitution pattern similar to that of a thymine ring. Nucleosides with a six-membered carbohydrate moiety have been considered over the past decades as the cornerstone for the development of effective, selective and nontoxic antiviral and antibiotic properties and as building blocks in nucleic acid synthesis. Summary: This article details the synthesis of 1-[2, 4-Dideoxy-4-C-hydroxymethyl-r-L- lyxopyranosyl] thymine (See Figure 2). Figure 1 shows what this compound is. The compound is labeled as 4 in Figure 2. Figure 1 Figure 2 Kelley Krueger Reagents used in this synthesis were as follows: (a) PhOC(S)Cl, DMAP, CH 3 CN; (b) -t ributylstannyl styrene, AIBN, benzene; (c) NMMO, OsO...
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