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-alpha-l-ribo-hexopyranoside in 35% yield over nine facile steps is described.
Timmons
Shannon C
SC
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, Canada B3H 4J3.
Jakeman
David L
DL
D003837:Deoxy Sugars / Q000737:chemistry*; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry*; D012210:Rhamnose / Q000737:chemistry; D013237:Stereoisomerism
D003837:Deoxy Sugars; D006601:Hexoses; C020615:digitoxose; D012210:Rhamnose