Abstract
Methanolysis of 2,4,6-tri- O-benzoyl-2,3-dibromo-3-deoxy- d-altrono-1,5-lactone gave methyl 3-bromo-3-deoxy-2,4,6-tri- O-benzoyl-α- d- ribo-hex-2-ulofuranosonate ( 3) and the anomeric mixture of the analogous 4,6-di- O-benzoyl derivative, having HO-2 free. Compound 3 was subjected to debromination with tributyltin hydride and tributyltin deuteride in the presence of 2,2′-azo-bisisobutyronitrile affording, respectively, the corresponding derivatives of 3-deoxy- d- erythro-2-hexulosonic acid and its 3-deuterio analog. The structure of the products and intermediates was established by spectroscopic methods and chemical transformations.
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