On the synthesis of the 2,6-dideoxysugar L-digitoxose
Shannon C Timmons1, David L Jakeman
1Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada B3H 4J3.
Abstract:
As deoxysugars are integral components of many natural products, the development of efficient chemical and enzymatic routes to prepare these compounds is of particular interest. Herein, we report a comparison of several synthetic methodologies used to prepare protected derivatives of the 2,6-dideoxysugar l-digitoxose. A novel, stereoselective synthetic route to efficiently access methyl 4-O-tert-butyldimethylsilyl-2,6-dideoxy-3-O-trimethylsilyl-alpha-l-ribo-hexopyranoside in 35% yield over nine facile steps is described.
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