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University of Toronto

1. Ward, Robert Massey. Synthesis and Glycosylation of Various Ceramide Derivatives via Borinic Acid Catalysis.

Degree: 2017, University of Toronto

Glycosphingolipids (GSLs) have become of increased interest due to recent realization that they may place a role in neurological diseases and cancer. Chemical synthesis of GSLs from simple building blocks requires efficient, yet selective methods to develop the major two components: ceramide and the carbohydrate. Much effort has been done to develop synthesis of the individual components; however the construction of the O-glycosidic bond that connects them has been plagued with regio- and stereoselectivity issues. In the past, both the ceramide and carbohydrate had to be chemically modified for the glycosylation step to occur with good selectivity and yields, but recently unprotected ceramides have been used with protected donors. Borinic acid catalysis has been an important advance in this field, allowing for higher yields and excellent β-selectivity to develop GSLs. This thesis describes the synthesis of various ceramide derivatives and their corresponding glycosylation by borinic acid catalysis.

M.Sc.

Advisors/Committee Members: Taylor, Mark S, Chemistry.

Subjects/Keywords: 0485

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Ward, R. M. (2017). Synthesis and Glycosylation of Various Ceramide Derivatives via Borinic Acid Catalysis. (Masters Thesis). University of Toronto. Retrieved from http://hdl.handle.net/1807/79139

Chicago Manual of Style (16th Edition):

Ward, Robert Massey. “Synthesis and Glycosylation of Various Ceramide Derivatives via Borinic Acid Catalysis.” 2017. Masters Thesis, University of Toronto. Accessed November 19, 2017. http://hdl.handle.net/1807/79139.

MLA Handbook (7th Edition):

Ward, Robert Massey. “Synthesis and Glycosylation of Various Ceramide Derivatives via Borinic Acid Catalysis.” 2017. Web. 19 Nov 2017.

Vancouver:

Ward RM. Synthesis and Glycosylation of Various Ceramide Derivatives via Borinic Acid Catalysis. [Internet] [Masters thesis]. University of Toronto; 2017. [cited 2017 Nov 19]. Available from: http://hdl.handle.net/1807/79139.

Council of Science Editors:

Ward RM. Synthesis and Glycosylation of Various Ceramide Derivatives via Borinic Acid Catalysis. [Masters Thesis]. University of Toronto; 2017. Available from: http://hdl.handle.net/1807/79139

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