Conversion of uracil derivatives to cytosine derivatives

Details Conversion of uracil derivatives to cytosine derivatives Conversion of uracil derivatives to cytosine derivatives

1986-05-27

1988-06-28

Sutto, Anton H.

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

Organic compounds

Carbohydrates or derivatives

536122, C07H 19067, C07H 1900

Patent

active

047540265

ABSTRACT:
A process is disclosed for producing a 4-O-sulfonyluracil derivative of the formula ##STR1## [wherein R.sup.1 is hydrogen, halogen, alkyl and alkoxy, R.sup.2 is glycosyl having protected hydroxyls; and --SO.sub.2 R.sup.3 is an organic sulfonyl] which comprises reacting an uracil derivative of the formula ##STR2## [wherein R.sup.1 and R.sup.2 are as defined above] with an organic sulfonylating agent of the formula R.sup.3 SO.sub.2 X [wherein R.sup.3 SO.sub.2 is an organic sulfonyl and X is halogen] in the presence of potassium carbonate. The obtained 4-O-sulfonyluracil is further subjected to amination. The processes are industrially adavantageous and produce cytosine derivatives such as cytidine in high yield.

REFERENCES:
Heinzscheit, Nucleotide Analogs, Syn. & Biological Function, Wiley-Interscience Publication, 1980.
Fox et al., J.A.C.S., 81, pp. 178-187 (1959).
Kaneko et al., Chem. Pharm. Bull., 20, pp. 1050-1053 (1972).

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