Synthesis of Enantiomers of Butane-1,2-diacetal-Protected Glyceraldehyde and of (R,R)-Butane-1,2-diacetal-Protected Glycolic Acid

Patrick Michel; Steven V. Ley

doi:10.1055/s-2003-40519

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Synthesis of Enantiomers of Butane-1,2-diacetal-Protected Glyceraldehyde and of (R,R)-Butane-1,2-diacetal-Protected Glycolic Acid

Patrick Michel, Steven V. Ley*
Department of Chemistry, University of Cambridge
Fax: Lensfield Road, Cambridge, CB2 1EW, UK; e-Mail: svl1000@cam.ac.uk;

Abstract

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Abstract

A convenient and scalable synthesis of enantiomers of butane-2,3-diacetal-protected glyceraldehyde was accomplished from d-mannitol and l-ascorbic acid, respectively. The R-aldehyde was additionally converted to the (R,R)-butane-2,3-diacetal glycolic acid building block 1.

Key words

diacetal - glyceraldehydes - α-hydroxy acid - d-mannitol - l-ascorbic acid

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References

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[α]_D of this aldehyde in CHCl₃ is not reliable because the value increases from -110 to -160 in two hours possibly due to an acid-catalysed decomposition. Nevertheless, the enantiomeric excess of 1 determined by chiral GC proved that the enantiomeric excess of 6 is at least 99%.