The first polymer-assisted solution-phase synthesis of deoxyglycosides.
[reaction--see text] A glycosylation protocol for the synthesis of 2-deoxyglycosides has been developed which is based on the use of polymer-bound reagents. Glycals are transformed into 2-iodoglycosyl acetates using polymer-bound bis(acetoxy)iodate(I) complex (1). Activation of the anomeric center is achieved by employing polymer-bound silyl triflate (2). In the presence of different glycosyl acceptors, 2-deoxy-2-iodoglycosides are generated in very good yields. Furthermore, it is shown that this method can be embedded in multistep sequences toward glycosylated testosterone and rhodinosyl-olivosyl-olivoside.
Kirschning
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Institut für Organische Chemie der Universität Hannover, Schneiderberg 1B, D-30167 Hannover, Germany. andreas.kirschung@oci.uni-hannover.de
Jesberger
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Schönberger
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D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D011108:Polymers; D013739:Testosterone / Q000031:analogs & derivatives / Q000138:chemical synthesis; D014312:Trisaccharides / Q000138:chemical synthesis / Q000737:chemistry
D006027:Glycosides; D007202:Indicators and Reagents; D011108:Polymers; D014312:Trisaccharides; D013739:Testosterone