Attempts were made to synthesize cleanly and efficiently a 3,6-branchpoint mannose monomer via three synthetic routes. This monomer was then to be used in a solution-phase synthesis of a high mannose-type nonasaccharide using a PEG soluble polymer support developed in our laboratory. The monomer was to meet the requirements of (1) stable protecting groups on positions 2 and 4; (2) easily cleavable groups on positions 3 and 6; (3) a group which is stable and a good donor on position 1. The key step in the synthesis of the first monomer, containing allyl groups on positions 3 and 6, involved using Ogawa's stannylation methodology. The key step in the second route involved benzylating a monomer containing two ester groups on positions 3 and 6 using Bundel's methodology. The third route, based on well established literature procedures, gave the desired compound in acceptable yield but with more purification effort. / Using a similar approach to that taken independently by Stork and Hindsgaul, attempts were made to construct $ beta$-glycosides using antimony as a temporary connector. (Abstract shortened by UMI.)
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.27290 |
| Date | January 1997 |
| Creators | Bubenik, Monica. |
| Contributors | Chan, T.-H. (advisor) |
| 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 | Master of Science (Department of Chemistry.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 001572067, proquestno: MQ29665, Theses scanned by UMI/ProQuest. |
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