ChemInform Abstract: Application of Sugar Phosphonates for the Preparation of Higher Carbon Monosaccharides.
Abstract
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ChemInform Abstract
Sugar phosphonates as (I), (VI),and (IX), which can be prepared in much higher yields and which are much more nucleophilic than previously used sugar phosphoranes, react with sugar aldehydes, e.g. (II) and (IV), to generate the appropriate enones with trans configuration of the double bond. Whereas reduction of enone (III) is accomplished in low selectivity, affording an inseparable mixture of sugar allylic alcohols, reduction of enones (VII) and (X), which have the carbonyl group placed at the α-position of the sugar ring, yields allylic alcohols (VIII) and (XI) in high stereoselectivity.
