Glycals 2-deoxy aldoses

A further example has been given of the synthesis of a 2-deoxy-aldose by the addition of water to a glycal, but, as this reaction is known to be accompanied by competing eliminations,1 it is being replaced in synthetic work by more-specific addition procedures, for example, methoxymercuration (see p. 210). From the 4-deoxy derivative of D-glucal, prepared by standard procedures from 2,3,6-tri-O-acetyl-4-deoxy-D-xy/o-hexopyranosyl bromide, 2,4-dideoxy-D-threo-hexose was obtained.35... 

The glycals, first reported by Fischer and Zach, were extensively investigated by Bergmann and Schotte. They are important intermediates for the interconversion of epimeric sugars and for the preparation of 2-deoxy-aldoses (Chapter II). 

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