β-Selective Glucosylation in the Absence of Neighboring Group Participation: Influence of the 3,4-O-Bisacetal Protecting System |
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Authors: | Crich David Subramanian Venkataraman Hutton Thomas K |
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Institution: | Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA |
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Abstract: | A 3,4-O-bisacetal 2,6-di-O-benzyl protected thioglucoside is converted to the corresponding glucosyl triflate with 1-benzenesulfinyl piperidine and trifluoromethanesulfonic anhydride. The moderate to excellent β-selectivity exhibited with this glucosyl triflate with a range of alcohols is generally higher than that observed with the more electronically disarmed corresponding 3,4-O-carbonate, for which a possible reason is advanced. |
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Keywords: | Glycosylation Bisacetal Glycosyl triflate Stereoselectivity Protecting group |
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