Abstract
1,2:5,6-Di-O-isopropylidene-alpha-D-glucofuranose by the sequence of mild oxidation, reduction, fluorination, periodate oxidation, borohydride reduction, and sulfonylation gave 3-deoxy-3-fluoro-1,2-O-isopropylidene-5-O-p-toluenesulfonyl-alpha-D-xylofuranose (5). Tosylate 5 was converted to thioacetate derivative 6, which after acetolysis gave 1,2-di-O-acetyl-5-S-acetyl-3-deoxy-3-fluoro-5-thio-D-xylofuranose (7). Condensation of 7 with silylated thymine, uracil, and 5-fluorouracil afforded nucleosides 1-(5-S-acetyl-3-deoxy-3-fluoro-5-thio-beta-D-xylofuranosyl) thymine (8), 1-(5-S-acetyl-3-deoxy-3-fluoro-5-thio-beta-D-xylofuranosyl) uracil (9), and 1-(5-S-acetyl-3-deoxy-3-fluoro-5-thio-beta-D-xylofuranosyl) 5-fluorouracil (10). Compounds 8, 9, and 10 are biologically active against rotavirus infection and the growth of tumor cells.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology*
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Antiviral Agents / chemical synthesis*
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Antiviral Agents / chemistry
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Antiviral Agents / pharmacology*
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Caco-2 Cells
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Drug Screening Assays, Antitumor
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Fluorouracil / chemistry
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Humans
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Intestines / cytology
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Intestines / drug effects
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Microbial Sensitivity Tests
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Molecular Structure
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Nucleosides / chemical synthesis*
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Nucleosides / chemistry
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Nucleosides / pharmacology*
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Rotavirus / drug effects
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Stereoisomerism
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Structure-Activity Relationship
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Thymine / chemistry
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Uracil / chemistry
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Xylose / analogs & derivatives*
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Xylose / chemistry
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Zidovudine / pharmacology
Substances
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3-fluoro-5-thio-xylofuranose
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Antineoplastic Agents
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Antiviral Agents
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Nucleosides
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Zidovudine
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Uracil
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Xylose
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Thymine
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Fluorouracil