Aluminum- and boron-mediated c-glycoside synthesis from 1,2-anhydroglycosides.
[reaction: see text]This letter describes a single flask strategy to the synthesis of alpha-C-glycosides from glycals. This protocol couples a glycal epoxidation reaction with a C-2 alkoxy-directed carbon-carbon bond-forming reaction.
Rainier
J D
JD
Department of Chemistry, The University of Arizona, Tucson 85721, USA. rainier@u.arizona.eduTI Aluminum- and boron-mediated C-glycoside synthescosides.
Cox
J M
JM
D000535:Aluminum / Q000737:chemistry; D001895:Boron / Q000737:chemistry; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D013696:Temperature
D004852:Epoxy Compounds; D006027:Glycosides; D007202:Indicators and Reagents; D000535:Aluminum; D001895:Boron