A stereoselective synthesis of xylitol |
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| Authors: | David Holland J.Fraser Stoddart |
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| Affiliation: | 1. Corporate Laboratory, Imperial Chemical Industries PLC, The Heath, Runcorn WA7 4QE UK;2. Department of Chemistry, The University Sheffield S3 7HF UK |
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| Abstract: | Rel-(2S, 3R, 4R)- (6) and rel-(2R,3R,4R)- (7) 1,2,5-triacetoxy-3,4-epoxypentanes have been obtained in seven steps starting from cyclopentadiene. Both diastereoisomers afford xylitol pentaacetate (8) selectively upon epoxide cleavage with acetate ion. In the case of (6), rel-(1s,3R,4r,5S)-3,-bisacetoxymethyl-1-methyl-2,6,7-trioxabicyclo- [2.2.1]heptane (11) has been isolated and characterised as an intermediate in the reaction. |
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