De novo synthesis of oligosaccharides using a palladium-catalyzed glycosylation reaction |
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Authors: | Babu Ravula Satheesh Zhou Maoquan O'Doherty George A |
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Institution: | Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA. |
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Abstract: | The natural all d- and/or unnatural all l-1,4- and 1,6-oligosaccharides were synthesized from furan alcohols using a palladium-catalyzed glycosylation reaction. The 1,4- and 1,6-alpha-manno-disaccharides were achieved in seven total steps starting from chiral furan alcohols. Similarly, 1,4- and 1,6-alpha-manno-trisaccharides were also synthesized in nine total steps. Key to the overall efficiency of this process was the use of highly diastereoselective palladium-catalyzed glycosylations, reductions, and dihydroxylations. |
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