Abstract
This chapter discusses the alkylation of monosaccharides using sodium hydride. Monosaccharides may be conveniently alkylated by using an alkyl halide—usually the bromide—in either N , N -dimethylformamide (DMF) or N -methyl-2-pyrrolidone containing suspended sodium hydride. In some alkylations, tetrahydrofuran has been employed as the solvent but it is unsuitable for general use as it is not a good solvent for relatively unsubstituted sugars. Both N , N -dimethylformamide (DMF) and N -methyl-2-pyrrolidone are good solvents for most carbohydrates and appear to enhance formation of the nucleophilic alkoxide ion. Neither solvent reacts significantly with sodium hydride at ambient temperature although degradation of DMF occurs above 70°. The method can be easily applied, provided that due care is exercised in the handling of the hydride and the excess of reagents are removed by the addition of dry methanol on completion.
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