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Synthesis of Novel Cyclobutane Nucleoside Analogues

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dc.contributor.advisorLee-Ruff, Edward
dc.creatorHassan, Muhammad Murtaza
dc.date.accessioned2018-03-01T13:50:22Z
dc.date.available2018-03-01T13:50:22Z
dc.date.copyright2017-06-02
dc.date.issued2018-03-01
dc.date.updated2018-03-01T13:50:21Z
dc.degree.disciplineChemistry
dc.degree.levelMaster's
dc.degree.nameMSc - Master of Science
dc.description.abstractA synthesis of cyclobutane nucleosides is described. The method involved the triflation of a -hydroxymethyl-cyclobutanone and its subsequent displacement by a 6-chloropurinyl anion to generate N-7 and N-9 regioisomers. The stereoselective reduction of the N-alkylated ketones yielded the cis-alcohols quantitatively and the geometric configuration was confirmed by spectroscopic data and X-ray diffraction. Photolysis of N-7 and N-9 coupled ketones was carried out in methanol using quartz tubes to promote ring-expansion isonucleoside products. Photolysis did not yield any ring-expansion or cycloelimination products, rather, the products are suspected to be cyclopropanes from decarbonylation of the ketones, since these are less polar and show shielding of protons in their corresponding NMR spectra, consistent with substituted cyclopropanes.
dc.identifier.urihttp://hdl.handle.net/10315/34283
dc.language.isoen
dc.rightsAuthor owns copyright, except where explicitly noted. Please contact the author directly with licensing requests.
dc.subjectChemistry
dc.subject.keywordsNucleoside analogues
dc.subject.keywordsAntiviral agents
dc.subject.keywordsAntitumor agents
dc.subject.keywordsOrganic chemistry
dc.subject.keywordsCyclobutanone
dc.subject.keywordsCyclobutane
dc.subject.keywordsCarboycylic
dc.subject.keywordsPhotochemistry
dc.subject.keywordsRing-expansion
dc.subject.keywordsReduction
dc.subject.keywordsStereospecific reduction
dc.subject.keywordsNMR
dc.subject.keywordsNuclear magnetic resonance spectroscopy
dc.subject.keywordsIR
dc.subject.keywordsInfrared spectroscopy
dc.subject.keywordsUV-Visible
dc.subject.keywordsUltra-violet visible spectroscopy
dc.subject.keywordsMS
dc.subject.keywordsMass spectroscopy
dc.subject.keywordsCycloelimination
dc.subject.keywordsDecarboxylation
dc.subject.keywordsCyclobutanol
dc.subject.keywordsCyclopropane
dc.subject.keywordsAlkene
dc.subject.keywordsFuranose
dc.subject.keywordsMitsunobu
dc.subject.keywordsN-alkylation
dc.subject.keywordsPurine
dc.subject.keywords6-chloropurine
dc.subject.keywordsPyrimidine
dc.subject.keywordsAlcohol
dc.subject.keywordsMedicine
dc.subject.keywordsDrugs
dc.subject.keywordsPhoton
dc.subject.keywordsSolvents
dc.subject.keywordsChromatography
dc.subject.keywordsDNA
dc.subject.keywordsRNA
dc.subject.keywordsCrystallography
dc.subject.keywordsCrystal structure
dc.subject.keywordsBiochemistry
dc.subject.keywordsNucleobases
dc.subject.keywordsNitrogenous bases
dc.subject.keywordsNucleic acids
dc.subject.keywordsModifications of nucleosides
dc.subject.keywordsKinases
dc.subject.keywordsSuffocation
dc.subject.keywordsTriflate
dc.subject.keywordsTriflation
dc.subject.keywordsMesylation
dc.subject.keywordsMesylate
dc.subject.keywordsTosylate
dc.subject.keywordsRegioisomer
dc.subject.keywordsN-9
dc.subject.keywordsN-7
dc.subject.keywordsTheoretical calculations
dc.titleSynthesis of Novel Cyclobutane Nucleoside Analogues
dc.typeElectronic Thesis or Dissertation

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