The synthesis of C-glycosides and higher monosaccharides employing 1,3-dipolar cycloaddition chemistry
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 py...
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University of Edinburgh
2004
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| Online Access: | http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.657082 |
| Summary: | 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). |
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