Method of producing nucleosides

C - Chemistry – Metallurgy – 07 – H

Patent

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C07H 19/00 (2006.01) C07H 19/06 (2006.01) C07H 19/12 (2006.01) C07H 19/16 (2006.01)

Patent

CA 2701856

Method of producing a free nucleoside compound, the compound 2'- deoxy-5- azacytidine (Decitabine) being excluded, by reacting a glycoside donor preferably a 1-halogen derivative, or 1-0-acyl, 1-0-alkyl, or an imidate preferably a trichloromethyl derivative, or a thio-alkyl derivative of a blocked monosaccharide or oligosaccharide preferably ribose and 2-desoxyribose derivatives with a protected nucleoside base, in a suitable anhydrous solvent and in the presence of a catalyst, and removing the protecting groups from said blocked nucleoside compound, wherein said catalyst is selected from the group comprising salts of an aliphatic sulphonic acid and/or salts a strong inorganic acid containing a non-nucleophilic anion.

L'invention concerne un procédé de production d'un composé nucléosidique libre, le composé 2'-désoxy-5-azacytidine (Décitabine) étant exclu, par la réaction d'un donneur de glycoside, de préférence un dérivé 1-halogéné, ou 1-O-acyle, 1-O-alkyle, ou un imidate, de préférence un dérivé trichlorométhyle, ou un dérivé thioalkylique d'un monosaccharide ou oligosaccharide, de préférence un ribose, bloqué, et de dérivés de 2-désoxyribose avec une base nucléosidique protégée, dans un solvant anhydre approprié et en présence d'un catalyseur, et l'élimination des groupes protecteurs dudit composé nucléosidique bloqué, ledit catalyseur étant sélectionné dans le groupe comprenant des sels d'un acide sulfonique aliphatique et/ou des sels d'un acide inorganique fort contenant un anion non nucléophile.

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