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A general method was developed on the basis of the Wittig reaction for the synthesis of trans-2,3-dehydro-2,3-dideoxy aldonic acids, which are key compounds for the synthesis of higher sugars.
The Wittig reaction with unprotected monosaccharides is accompanied by the formation of a byproduct, whose structure was proved rigorously for the case of the condensation with D-galactose.
With the condensation of ethyl (triphenylphosphoranylidene)acetate with 2,3,4,6-tetra-O-acetyl-α-D-galaetopyranose taken as example it was shown that acetates of monosaccharides also react smoothly in the Wittig reaction with formation of partially acetylated trans-2,3-dehydro-2,3-dideoxy aldonic acids.
KeywordsAcetate Sugar Ethyl Monosaccharide High Sugar
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