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Synlett 1993; 1993(4): 264-266
DOI: 10.1055/s-1993-22425
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Highly Stereoselective Synthesis of α-L-Olivomycosides via Trimethylsilyl Triflate Mediated Glycosidations of 1-O-Acetyl-4-O -isobutyryl-2,6-dideoxy-2-iodo-3-C-methyl-α-L-mannopyranose

William R. Roush* , Karin Briner, David P. Sebesta
  • *Department of Chemistry, Indiana University, Bloomington, Indiana 47405, USA
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Publication History

Publication Date:
19 March 2002 (online)

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A highly stereoselective synthesis of α-L-olivomycosides via trimethylsilyl triflate mediated glycosidations of 2-iodoolivomycarosyl-1α acetate 4 is described. Evidence is presented that the intermediate iodonium ion 20 is configurationally stable under the reaction conditions.