Stereospecific Synthesis of 1,2-trans-1-Phenylthio-β-D-Disaccharides Under Phase Transfer Catalysis
- 1 January 1991
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1991 (09) , 734-736
- https://doi.org/10.1055/s-1991-26559
Abstract
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.Keywords
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