Improved Syntheses of Both Enantiomers of 1,2,5,6-Diepoxyhexane from (2S,5S)-1,2,5,6-Hexanetetrol
- 1 January 1992
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1992 (10) , 989-994
- https://doi.org/10.1055/s-1992-26286
Abstract
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.Keywords
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