Synthesis of furanose derivatives of 3-deoxy-D-erythro-2-hexulosonic acid and their 3-bromo and 3-deuterio analogs.
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-alpha-D-ribo-hex-2-ulofuranosonat e (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.
Di Nardo
C
C
Universidad de Buenos Aires, Ciudad Universitaria, Argentina.
Varela
O
O
D001419:Bacteria / Q000737:chemistry / Q000378:metabolism; D005663:Furans / Q000737:chemistry*; D005942:Gluconates / Q000737:chemistry; D007661:Ketoses / Q000138:chemical synthesis* / Q000737:chemistry; D013400:Sugar Acids / Q000737:chemistry
D005663:Furans; D005942:Gluconates; D007661:Ketoses; D013400:Sugar Acids; C012991:galactonic acid; C068286:3-deoxyhexulose