172293-74-2Relevant academic research and scientific papers
Synthesis of a 3-Deoxy-D-arabino-2-heptulosonic Acid Derivative
Devianne, Gerard,Escudier, Jean-Marc,Baltas, Michel,Gorrichon, Liliane
, p. 7343 - 7347 (2007/10/03)
The synthesis of a selectively protected 3-deoxy-D-arabino-2-heptulosonic acid, 9, from a non-carbohydrate precursor was achieved in six steps (19percent yield) from a chiral, γ,δ-epoxy β-hydroxy ester, 3a, readily available from the corresponding α,β-epoxy aldehyde.The product was obtained through a Lewis acid-mediated stereocontrolled lactonization of 3a followed by a two-step procedure: synthesis of Weinreb's amide 5a and lithiothiazole nucleophilic attack allowing the introduction of the masked aldehydo frame.
