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Preparation of enantiomeric erythro and threo 1 2 3 pentanetriols by an enzymatic racemate resolution


, : Preparation of enantiomeric erythro and threo 1 2 3 pentanetriols by an enzymatic racemate resolution. Liebigs Annalen der Chemie (7): 629-632

(2R,3S)- and (2S,3R)-erythro- (9a/9b) as well as (2R,3R)- and (2S,3S)-threo-1,2,3-pentanetriol (10a/10b) are synthesized from the rac. trans- and cis-isomeric 2,3-epoxypentyl butyrates 5/6 by Lipase-controlled racemate resolution followed by regioselective ring opening of both the chiral epoxy alcohols 3a/3b and 4a/4b, respectively. Whereas the erythro-triols 9a and 9b are obtained in very good enantiomeric excesses, the reaction sequence yields poor ee values in the case of the threo-triols 10a and 10b.

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