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- W2484112844 abstract "Publisher Summary This chapter discusses the preparation of methyl 3-deoxy-3-nitrohexopyranosides from methyl glycosides through nitromethane cyclization. Periodate oxidation of methyl aldosides gives sugar dialdehydes, which react with nitromethane in a twofold Henry reaction so as to furnish methyl 3-deoxy-3-nitro-aldopyranosides. One or two of the stereoisomeric nitroglycosides that arise in the cyclization of a given dialdehyde are usually formed in marked preponderance, which facilitates their isolation, although minor isomers have also been isolated on some occasions. In the method, a solution of 42.8 g of sodium metaperiodate in 500 ml of water is cooled to about 5° in an ice and water bath, and 19.4 g of crystalline methyl β- d -glucopyranoside is introduced in portions over a period of 10 min with continual swirling. The reaction mixture is then brought to ∼ 25° by brief immersion of the flask in warm water and is thereafter kept in a dark place for 3 hours. During this period, a total of 90 ml of 1 M sodium bicarbonate solution is added in several portions, care being taken that the pH of the reaction mixture does not exceed 5–6 at any time. Soluble sodium iodate is sparingly deposited during the oxidation. This procedure is repeated if dissolution of the resulting syrup in ethanol still causes an appreciable quantity of salt to separate." @default.
- W2484112844 created "2016-08-23" @default.
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- W2484112844 date "1972-01-01" @default.
- W2484112844 modified "2023-09-26" @default.
- W2484112844 title "Methyl 3-Deoxy-3-nitrohexopyranosides" @default.
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- W2484112844 doi "https://doi.org/10.1016/b978-0-12-746206-6.50049-7" @default.
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