Branched-chain Sugars. IV. Synthesis of 5,6-Dideoxy-5-C-hydroxymethyl-1,2-O-isopropylidene-6-C-nitro-3-O-substituted-α-d-glucose Derivatives
- 1 October 1973
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 46 (10) , 3207-3209
- https://doi.org/10.1246/bcsj.46.3207
Abstract
Addition of nitryl iodide to 5-deoxy-1,2,O-isopropylidene-3-O-methyl-5-C-methylene-6-O-substituted-α-d-xylo-hexofuranoses (3 and 4), and subsequent hydrogenation with sodium borohydride gave a mixture of the corresponding 5,6-dideoxy-5-C-hydroxymethyl-6-C-nitro derivatives of d-gluco and l-ido forms. The configuration of both isomers were determined by intramolecular cyclization into the corresponding nitrocyclohexanetetrols. The ratios of d-gluco to l-ido product were 1: 2 in the case of 6-O-trityl derivative (3) and 4: 5 in the case of 6-O-benzyl derivative (4), respectively.This publication has 2 references indexed in Scilit:
- Addition of pseudohalogens to unsaturated carbohydrates. III. Synthesis of 3-deoxy-3-C-nitromethyl-D-allose, a branched-chain nitro sugarCanadian Journal of Chemistry, 1969
- Periodate Oxidation in the Synthesis of Some Partially Methylated Sugars1Journal of the American Chemical Society, 1955