The conversion of 8,2'-S-anhydroadenosine to adenosine was studied in order to determine the feasibility of using 8,2'-S-anhydropurine nucleosides for oligoribonucleotide synthesis. Sulfoxide derivatives of 8,2'-S-anhydroadenosine were prepared efficiently; however when they were subjected to Pummerer reaction conditions in an attempt to introduce a 2'-substituent, extensive decomposition occurred. / The synthesis of t-butyldimethylsilyl derivatives of cytidine and guanosine nucleosides was accomplished. Preparations were fast and simple, and most of the desired 2',5' diprotected nucleosides were obtained in greater than 50% yield from the nonsilylated nucleosides. Using the phosphorodichlorodite procedure, silylated nucleosides were easily incorporated into ribonucleotides. In addition to 3',5'-linked ribonucleotides, 2',5'- and symmetrically linked ribonucleotides were also prepared. ('1)H, ('13)C and ('31)P nuclear magnetic resonance spectroscopy was utilized in elucidating the structure of ribonucleotides; enzyme degradations on the completely deprotected ribonucleotides confirmed the position of the phosphate linkages.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.68515 |
| Date | January 1979 |
| Creators | Schifman, Aria Libi. |
| 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: 000089954, proquestno: AAINK50556, Theses scanned by UMI/ProQuest. |
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