Synthesis of C-aryl and C-alkyl glycosides using glycosyl phosphates |
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| Authors: | Palmacci E R Seeberger P H |
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| Institution: | Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA. |
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| Abstract: | reaction: see text] Mannosyl and glucosyl phosphate donors were successfully used in constructing C-aryl linkages common to many natural products via a Lewis acid induced Fries-like rearrangement. The rearrangement was stereo- and regiospecific, yielding only one C-glycoside product. C-Alkyl glycoside carbohydrate mimetics were generated by using silicon-derived C-nucleophiles and glycosyl phosphates. |
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