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Synthesis 1991; 1991(9): 734-736
DOI: 10.1055/s-1991-26559
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Stereospecific Synthesis of 1,2-trans-1-Phenylthio-β-D-Disaccharides Under Phase Transfer Catalysis

François D. Tropper* , Fredrik O. Andersson, Chantal Grand-Maître, René Roy
  • *Department of Chemistry, University of Ottawa, Ottawa, Ontario, K1N 6N5, Canada
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Publication Date:
29 April 2002 (online)

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Peracetylated α-glycobiosyl bromides 1-5 derived from commercially available disaccharides, were transformed with complete anomeric stereocontrol into phenyl 1,2-trans-1-thio-β-D-glycobiosides 6-10 by nucleophilic displacement under phase transfer catalyzed glycosidation in 77-92% yields. The reaction proceed rapidly for most bromides in dichloromethane, but failed under similar conditions, to provide complete conversion of the melibiosyl bromide 4 into the S-phenyl thioglycoside 9. Nevertheless, the reaction gave good results when performed in toluene or ethyl acetate.