On the synthesis of the 2,6-dideoxysugar l-digitoxose

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-α- l- ribo-hexopyranoside in 35% yield over nine facile steps is described.