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Total synthesis of methyl 8(S)-, 9(S)-, 11(S)- and 12(S)- hydroxyeicosatetraenoates & of oligosaccharides from Haemophilus influenzae type B / Total syntheses of methyl 8(S)-, 9(S), 11(S)- and 12(S)- hydroxyeicosatetraenoates and of oligosaccharides from Haemophilus influenzae type B.

A general approach to the asymmetric syntheses of HETEs in both enantiomeric forms was developed. The syntheses of 8(S)-, 9(S)-, 11(S)- and 12(S)-HETE methyl esters, starting from D-arabinose, were accomplished. / A practical approach to the solution synthesis of fragments from Haemophilus influenzae type b capsular polymer was established, which opens a route to the development of a new vaccine against meningitis. The major aspects of this approach, stereocontrolled glycosidation, selective protection and deprotection, and efficient phosphorylation were detailed. The normal solution syntheses of the mono-, di- and tetrasaccharides were accomplished. / A new class of spacer for the linkage of the oligosaccharide with a protein was introduced. The spacer and the spacer-linked tetrasaccharide were prepared.

Identiferoai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.75423
Date January 1987
CreatorsWang, Zhi Yuan
PublisherMcGill University
Source SetsLibrary and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada
LanguageEnglish
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation
Formatapplication/pdf
CoverageDoctor of Philosophy (Department of Chemistry.)
RightsAll items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated.
Relationalephsysno: 000561149, proquestno: AAINL44255, Theses scanned by UMI/ProQuest.

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