Alditols reactivity

As shown in Scheme 1, the alditols studied herein have different chain lengths and/or stereochemistry. Given the inherent selectivity of enzymes, it was anticipated that N435-catalyzed polyesterification of these substrates would occur at different rates. However, the relative order of their reactivity during polymerization reactions was unpredictable. 

Using two model oligosaccharide alditols, factors affecting the reactivity of 2-acetamido-2-deoxy-hexopyranosides in the hydra-zlnolysis-nitrous acid deamination sequence have been Investigated. Hydrazinolysis in the presence of hydrazinium sulphate led to virtually quantitative N-deacetylation. Another reference to this procedure can be found in Chapter 10. 

Formaldehyde, as the most reactive aldehyde, undergoes Cannizzaro reaction even with aldehydes that have a hydrogen atom at the carbon. Formaldehyde also reacts to some extent with aldoses that are reduced to sugar alcohols (alditols) and formaldehyde is oxidised to formic acid (Figure 4.69). Reaction of formaldehyde with D-glucose yields D-glucitol, reaction with D-glyceraldehyde... 

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