In our investigation of the substrate specificity of 2-deoxy-n-ribose kinase isolated from Salmonella typhimurium, we required 2-deoxy-nribose (2-deoxy-L-erythro-pentose)
(1) and 2-deoxy-D-xylose (2-deoxyn-threo-pentose)
(2). Of the known methods for the preparation of these sugars (3, 4), the glycal method has been used most extensively. The syntheses involve several lengthy steps starting from L-arabinose for 2-deoxy-L-ribose (1, 3, 5) and from n-xylose for 2-deoxy-n-xylose (2, 6, 7), and the best reported yields are not greater than 10% (5). It seemed to us that an easier synthetic route to these 2-deoxypentoses might take advantage of the high yields of the methyl 2-deoxy-cu,,p-n-hexofuranosides obtained by treating commercially available %deoxy-D-galactose (2deoxy-n-lyxo-hexose) and 2-deoxy-n-glucose (2-deoxy-n-arabino-hexose) , respectively, with methanolic HCl (8, 9). Periodate oxidation of the furanosides, followed by sodium borohydride reduction of the resulting aldehydes and mild acid hydrolysis gave 2-deoxy-L-ribose and !&deoxy-Dxylose in 55% and 44% yields, respectively. 2-Deoxy-L-ribose was identified by paper chromatography, GLC of the alditol acetate, and formation of the 2-deoxy-L-ribose "anilide" derivative. 2-Deoxy-n-xylose was identified by paper chromatography.