Preparation of diacyl derivatives of 2'-deoxy-5-fluorouridine vi

Details Preparation of diacyl derivatives of 2'-deoxy-5-fluorouridine vi Preparation of diacyl derivatives of 2'-deoxy-5-fluorouridine vi

1989-04-21

1991-05-07

Shen, Cecilia

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

544313, C07H 1906, C07D23954

Patent

active

050138286

ABSTRACT:
2'-Deoxy-3',5'-diacyl-5-fluorouridines useful as antitumor medicines or intermediates thereof are easily and efficiently obtained by first fluorinating 2'-deoxyuridine in aqueous solution with fluorine gas to thereby form 2'-deoxy-5,6-dihydro-5-fluoro-6-hydroxyuridine, which is a novel compound, and reacting this compound with a carboxylic acid anhydride or halide R--CO--X, where R is an aliphatic group having not more than 20 carbon atoms or a substituted or unsubstituted phenyl group, and X is an acyloxy group RCO.sub.2 or a halogen atom. In the initial fluorination reaction the aqueous solution may contain a carbonate (or a hydrogen carbonate) or a lower fatty acid or its salt to capture hydrogen fluoride formed by the reaction. The next acylating reaction can be promoted by carrying out the reaction in the presence of an organic base such as pyridine.

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