Synthesis of C-aryl and C-alkyl glycosides using glycosyl phosphates.
[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.
Palmacci
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ER
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Seeberger
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PH
D015195:Drug Design; D006027:Glycosides / Q000138:chemical synthesis*; D018716:Molecular Mimicry; D013329:Structure-Activity Relationship
D006027:Glycosides