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Title: The synthesis of C-glycosides and higher monosaccharides employing 1,3-dipolar cycloaddition chemistry
Author: McMillan, Keith G.
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2004
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The sugar-derived alkenes were prepared using three methods; in the first hex-5-enofuranoses were generated in good yields from the corresponding 5,6-dimesylates using Tipson-Cohen conditions; the second employed an aprotic Bamford-Stevens reaction to give the 1-methylene sugar from the analogous pyranosyl tosylhydrazone. The final approach gave a series of 1-methylene sugars in moderate to good yields (50-82%) by the methylation of sugar lactones with dimethyl titanocene (Petasis Reagent).
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available