Abstract
This chapter discusses various applications in the carbohydrate field of reductive desulfurization by Raney nickel. Reductive desulfurization with Raney nickel is a reaction that requires but the simplest of techniques, is carried out under rather mild conditions, and affords relatively good yields; it is a standard and well-recognized reaction, having found use in practically all the various fields of organic chemistry. The chapter discusses Raney nickel's applications in sugar fields. Desulfurization carried out in aqueous alcohol has been observed to give rise to acetaldehyde; in view of the well-known dehydrogenating action of Raney nickel it seems likely that the solvent may play a part as a hydrogen donor in the reaction. In practice the sulfur-containing derivative is dissolved or suspended in a suitable solvent, treated with a sufficient quantity of Raney nickel, and either left at room temperature or heated under reflux, recovery of the product being effected by concentration of the liquid phase. The utility of Raney nickel desulfurization in solving problems of configuration in the sugar series is demonstrated in the ω-desoxyglycitol series. Reductive desulfurization with Raney nickel of the mercaptolysis products of streptomycin has supplied one of the keys to the elucidation of the structure and configuration of that antibiotic.
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