72599-55-4Relevant academic research and scientific papers
Base-Catalyzed Rearrangement of 6-Bromo-3,6-dideoxyaldohexono-1,4-lactones
Bock, Klaus,Lundt, Inge,Pedersen, Christian
, p. 163 - 171 (2007/10/02)
Upon treatment of 3-deoxy-D-arabino and 3-deoxy-D-xylo-hexono-1,4-lactone with hydrogen bromide in acetic acid (HBA), 6-bromo-3,6-dideoxy-D-arabino- and 6-bromo-3,6-dideoxy-D-xylo-hexono-1,4-lactone are produced.When reacted with anhydrous potassium carbonate in acetone the two bromodeoxylactones are converted into epoxides.Exposed to excess aqueous potassium hydroxide, the bromodeoxylactones, or the epoxides, rearrange to give 3-deoxy-L-ribo- and 3-deoxy-L-lyxo-hexono-1,4-lactone.Consequently, inversion at both C-4 and C-5 has taken place.In both cases, considerable amounts of anhydrides are formed along with the lactones.The mechanism of the base-induced rearrangements is discussed.The various 6-bromodeoxylactones undergo hydrogenolysis to give the corresponding 3,6-dideoxyhexono-1,4-lactones.On reduction, the 3,6-dideoxy-D-arabino-hexono-1,4-lactone affords 3,6-dideoxy-D-arabino-hexose (tyvelose).
