ES301738A1 - A procedure for the obtaining of 1-glicosil-5-azacitosinas. (Machine-translation by Google Translate, not legally binding) - Google Patents

Abstract

A process for the preparation of 1-glycosyl-5-azacytosines of the general formula I: ** (See formula) ** wherein R 1 represents a glycosyl or peracyl-glycosyl residue and R 2 represents a hydrogen atom or an alkyl group containing 1-4 carbon atoms; in the same formula R3 and R4 (R3 may be the same as or different from R4) represents hydrogen atoms or alkyl groups containing 1-4 carbon atoms, or aralkyl groups, for example, a benzyl group optionally substituted on the benzene ring, The process comprises acting on the esters of the glycosyl isocyanates of the general formula: R1 - N = C = O (II) where R1 is a peracylglycosyl, with O-alkylisoureas of the general formula V, ** (See formula) ** where R 5 represents an alkyl group containing 1-4 carbon atoms, thus forming 1-acylglycosyl-4-alkylisobiurets of the general formula III, ** (See formula) ** where R1 represents a peracylglycosyl residue and R5 represents the same as in formula V; condensing the latter derivatives with orthoesters of aliphatic acids of the general formula VI, R2 - C (OR6) 3 (VI) wherein R2 represents the same as in formula I and R6 represents a methyl or ethyl group, thus forming 1-acylglycosyl-4-alkoxy-2-oxo-1,2-dihydro-1,3,5-triazines of general formula IV , ** (See formula) ** R3 - NH - R4 (VII) where R3 and R4 represent the same as in formula I, thus forming 1-acyl glycosyl 5-azacytosine derivatives; and, finally, subjecting the latter derivatives to an alcoholysis, preferably by the action of methanol in the presence of sodium methoxide or an ammonolysis, preferably with ammonia in ethanol. (Machine-translation by Google Translate, not legally binding)