A versatile and stereocontrolled route to pyranose and furanose C-glycosides.
[reaction: see text] The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.
Harvey
Joanne E
JE
Department of Chemistry, University of York, Heslington, York YO10 5DD, UK. joanne.harvey@vuw.ac.nz
Raw
Steven A
SA
Taylor
Richard J K
RJ
D002384:Catalysis; D005663:Furans / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry*; D013237:Stereoisomerism
D005663:Furans; D006027:Glycosides; D007202:Indicators and Reagents; D011714:Pyrans; D010165:Palladium