In light of the remarkable antiviral activity of acyclic nucleoside analogues such as that of BIOLF-62 against the herpes viruses, a number of products in which heterocyclic bases were coupled to the active acyclic sugar moiety were prepared and submitted for biological testing. / Various dimethoxytritylated and t -butyldimethylsilylated derivatives of arabinoadenosine were prepared and fully characterised by $ sp1$H and $ sp{13}$C NMR spectroscopy. $ sp{29}$Si INEPT as well as $ sp{29}$Si-$ sp1{ rm H}$ correlated NMR were used to study various t -butyldimethylsilyl and triisopropylsilyl substituted ribonucleosides. / In an effort aimed at the development of new and better nucleoside protecting functions, the 2,4-dinitrobenzenesulfenyl group which is stable to both acidic and basic conditions, was used for $5 sp prime$-hydroxyl protection of ribonucleosides and its compatibility with the phosphodichoridite nucleoside coupling procedure was investigated. The nitrobenzenesulfenyl group was used in conjunction with the dimethoxytrityl group for $2 sp prime$-hydroxyl protection in the synthesis of a UpU dimer. The latter was fully characterised by enzymatic degradation and HPLC analysis of the products.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.75365 |
| Date | January 1986 |
| Creators | Boisvert, Suzanne, 1955- |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Doctor of Philosophy (Department of Chemistry.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 000417950, proquestno: AAINL38339, Theses scanned by UMI/ProQuest. |
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