Item – Theses Canada

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OCLC number
429725034
Link(s) to full text
LAC copy
LAC copy
Author
Ingram, Laura J.(Laura Jane),1980-
Title
The synthesis of sulfated carbohydrates using 2,2,2-trichloroethoxysulfuryl imidazolium triflates.
Degree
M. Sc. -- University of Waterloo, 2006
Publisher
Ottawa : Library and Archives Canada = Bibliothèque et Archives Canada, [2007]
Description
2 microfiches
Notes
Includes bibliographical references.
Abstract
The synthesis of an entirely new class of sulfating agents in the form of 2,2,2-trichloroethoxysulfuryl-'N'-methylimidazolium triflate is reported. This reagent was shown to be highly effective for incorporating trichloroethyl (TCE) protected sulfate groups into carbohydrates. The resulting TCE-protected sulfodiester carbohydrates were stable to a wide range of conditions including protecting group manipulations, anomeric activations and coupling conditions. The TCE group could be readily removed under mild conditions that do not affect most other protecting groups commonly used in carbohydrate chemistry or glycosidic linkages. These results indicate that monosaccharides bearing TCE-protected sulfate groups can be used as building blocks for the synthesis of sulfated oligosaccharides. This route to sulfated oligosaccharides represents a significant improvement over current approaches.
ISBN
9780494237267
0494237260