Improvements for the preparation of L-idose from D-glucose

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Abstract
L-Idose (10) was prepared via its 1,2-O-isopropylidene derivative (9). The latter was prepared by means of the known principle of inverting the configuration of C-5 in sulfonic esters derived from 1,2-O-isopropylidene-α-D-glucofuranose, but a number of new intermediates and variations in procedure were studied in order to achieve practical improvements. Starting compounds were the 3,5-di-p- toluenesulfonate (1), the 3-methanesulfonate-5-p-toluenesulfonate (4), and the 5-p-toluenesulfonate (7) of 6-O-benzoyl-1,2-O-isopropylidene-α-D-glucofuranose, and intermediates were the 3-p-toluene-sulfonate-5-acetate (2), the 3-methanesulfonate-5-acetate (5), and the 3,5-diacetate (8) of 6-O-benzoyl-1,2-O-isopropylidene-β-L-idofuranose. Compound 8 was converted into 9 directly, whereas 2 and 5 gave 9 by sodium reduction of their 5,6-deacylated derivatives 3 and 6.

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