PDXylopyranosealdehydoDXylose

Scheme 2.13 Acquisition of D-xylose from xylans in woody materials.

Like d-glucose and d-fructose, however, d-xylose can be utilized—chemically or microbially—to generate a variety of interesting five-carbon chemicals other than furfural (vide supra) or xylitol, a noncaloric sweetener,100 both being directly produced from xylan hydrolysates, that is, without the actual isolation of the sugar. Other readily accessible intermediate products of high preparative utility (Scheme 2.14) are the open-chain fixed dithioacetal,101 the d-xylal,102 and d-hydroxy-xylal esters,103 or pyrazol or imidazol N-heterocycles with a hydro-philic trihydroxypropyl side chain.89

Furfural

Furfural

OH Xylitol

OH OH

1.RC1

2.HBr

OH SEt

A Zn/HOAc

RO.X.OR

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