80483-21-2Relevant academic research and scientific papers
On the synthesis of the 2,6-dideoxysugar l-digitoxose
Timmons, Shannon C.,Jakeman, David L.
, p. 2695 - 2704 (2007)
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.
Syntheses of Selectively Alkylated Enol Ethers in the L-ribo Series
Koepper, Sabine,Lundt, Inge,Pedersen, Christian,Thiem, Joachim
, p. 531 - 536 (2007/10/02)
The reduction of enulose 1a predominantly leads to L-digitoxal (3a), although this method presents a sluggish reaction with moderate yields.In contrast, the preparation from L-digitoxose (4a) in a three-step one-pot procedure represents an advantageous approach.Regioselective 3- or 4-O-alkylations are achieved by phase-transfer catalysis method or via stannylidene intermediates to give monosaccharide precursors of the L-ribo series valuable for further interglycosidic linking.
