DSpace Repository

Synthesis of Novel Cyclobutane Nucleoside Analogues

Synthesis of Novel Cyclobutane Nucleoside Analogues

Show full item record

Title: Synthesis of Novel Cyclobutane Nucleoside Analogues
Author: Hassan, Muhammad Murtaza
Abstract: A 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.
Subject: Chemistry
Keywords: Nucleoside analogues
Antiviral agents
Antitumor agents
Organic chemistry
Cyclobutanone
Cyclobutane
Carboycylic
Photochemistry
Ring-expansion
Reduction
Stereospecific reduction
NMR
Nuclear magnetic resonance spectroscopy
IR
Infrared spectroscopy
UV-Visible
Ultra-violet visible spectroscopy
MS
Mass spectroscopy
Cycloelimination
Decarboxylation
Cyclobutanol
Cyclopropane
Alkene
Furanose
Mitsunobu
N-alkylation
Purine
6-chloropurine
Pyrimidine
Alcohol
Medicine
Drugs
Photon
Solvents
Chromatography
DNA
RNA
Crystallography
Crystal structure
Biochemistry
Nucleobases
Nitrogenous bases
Nucleic acids
Modifications of nucleosides
Kinases
Suffocation
Triflate
Triflation
Mesylation
Mesylate
Tosylate
Regioisomer
N-9
N-7
Theoretical calculations
Type: Electronic Thesis or Dissertation
Rights: Author owns copyright, except where explicitly noted. Please contact the author directly with licensing requests.
URI: http://hdl.handle.net/10315/34283
Supervisor: Lee-Ruff, Edward
Degree: MSc - Master of Science
Program: Chemistry
Exam date: 2017-06-02
Publish on: 2018-03-01

Files in this item



This item appears in the following Collection(s)