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- W2017106961 abstract "Addition of the alkyl Grignard reagents methylmagnesium iodide and ethylmagnesium bromide to the aldehyde 3-O-benzyl-1,2-O-isopropylidene-α-d-xylo-pentodialdo-1,4-furanose (1) gave a preponderance of the corresponding 6-deoxy- and 6,7-dideoxy-l-ido derivatives (2 and 3). Oxidation of these alcohols with chromic acid gave the 5-keto derivatives 6 and 7 in high yield. The benzyl group of 6 was cleaved by catalytic hydrogenolysis, and acid-catalyzed hydrolysis of the isopropylidene group afforded the delta-dicarbonyl monosaccharide 6-deoxy-d-xylo-hexos-5-ulose (10). The same sequence applied to 7 gave 6,7-dideoxy-d-xylo-heptos-5-ulose (11). An alternative route to 8 consisted in reversing the order of the oxidation and hydrogenolysis steps, starting with 2 or its d-gluco isomer 4. In this sequence, chromic acid was used for selectively oxidizing the 5- (rather than the 3-) hydroxyl group of the l-idofuranose and d-glucofuranose derivatives 12 and 13." @default.
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- W2017106961 title "A new synthesis of the cyclitol ring-system" @default.
- W2017106961 doi "https://doi.org/10.1016/s0008-6215(00)81589-x" @default.
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