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Synthesis 1991; 1991(9): 734-736
DOI: 10.1055/s-1991-26559
DOI: 10.1055/s-1991-26559
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
Stereospecific Synthesis of 1,2-trans-1-Phenylthio-β-D-Disaccharides Under Phase Transfer Catalysis
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Publikationsverlauf
Publikationsdatum:
29. April 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/199109/lookinside/thumbnails/10.1055-s-1991-26559-1.jpg)
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.