Improved syntheses of both enantiomers of 1,2,5,6-diepoxyhexane from (2S,5S)-1,2,5,6-hexanetetrol

Article abstract of DOI:10.1055/s-1992-26286

Several methods for the preparation of (2R,5R)- and (2S,5S)-1,2,5,6-diepoxyhexane (2) from 3,4-dideoxy-D-threo-hexitol [(2S,5S)-1,2,5,6-hexanetetrol (1)] as a single common chiral synthon are described. Among these methods, the methods via (2S,5S)-1,6-bis(pivaloyloxy)-2,5-hexanediol and (2S,5S)-2,5-bis(benzoyloxy)-1,6-dibromohexane, both derived from 1, provide the best results in terms of the selectivity, yield, and optical purity for the preparation of (R,R)-2 and (S,S)-2, respectively.