GB1010059A - - Google Patents

Abstract

The invention comprises: (a) compounds of the general formula <FORM:1010059/C2/1> wherein R1 represents an oxygen atom, R2 represents a hydrogen atom or a methyl radical, and R3 represents a hydrogen atom or, when R2 = CH3, an acetyl radical, or wherein R1 represents a sulphur atom, R2 represents a phenyl, benzyl or ethyl radical or an alkyl radical of more than 3 carbon atoms, and R3 represents a hydrogen atom or, when R2=C2H5, an acetyl radical; (b) the preparation (in crude form) of the compound in which R1=O and R2=R3=H (i.e. 3-C-hydroxymethyl-3,5-didesoxy -L-lyxofuranose) by reducing an aqueous solution of 3-C-hydroxymethyl-3,5-didesoxy-L-lyxono-q -lactone with sodium amalgam while maintaining the pH of the reaction medium within the range 2 to 6, or with sodium borohydride while maintaining the pH of the reaction medium within the range 2-4; (c) the preparation of the compounds in which R1=S1 R2=phenyl, benzyl or alkyl or more than 3 carbon atoms, and R3=H, by reacting the product of (b) with a compound R2SH and hydrochloric acid; (d) the preparation of the compound in which R1=S, R2=C2H5 and R3= acetyl, by reacting the product of (b) with ethyl mercaptan and hydrogen chloride and then acetylating the product; (e) the preparation of the compound in which R1=O, R2=CH3 and R3=acetyl, by reacting the product of (b) with methanolic hydrogen chloride and then acetylating the product; and (f) the production of purified 3-C-hydroxymethyl-3,5-didesoxy-L-lyxofuranose by demercaptalating a product of (c) with mercuric chloride and mercuric oxide, or deacetylating the product of (d) with barium methoxide and then demercaptalating the product with mercuric chloride and cadmium carbonate, or deacetylating the product of (e) with barium methoxide and then demethylating the product with hydrochloric acid.