Process for producing 3'-deoxy-3-'-fluorothymidine

Details Process for producing 3'-deoxy-3-'-fluorothymidine Process for producing 3'-deoxy-3-'-fluorothymidine

1991-07-29

1992-11-24

Tsang, Cecilia

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

Organic compounds

Carbohydrates or derivatives

435 85, 435 87, C07D23956

Patent

active

051663279

ABSTRACT:
This invention provides a process for producing 3'-deoxy-'-fluorothymidine, which comprises allowing 3'-deoxy-'-fluoro-5'-mesylthymidine (the stating material) to react with an acetylating agent, selected from the group consisting of alkali metal salts of acetic acid, amine salts of acetic acid and ammonium acetate, in an aprotic, ploar solvent to form the 5'-acetyl derivative, and ammonium acetate, in an aprotic, polar solvent to form the 5'-acetyl derivative, and eliminating the 5'-acetyl group from this intermediate, thereby giving the objective 3'-deoxy-'-fluorothymidine.
According to the process of this invention described above, the 5'-mesyl derivative can be efficiently acetylated, and 3'-deoxy-'-fluorotymidine can be obtained in a high yield.

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Pudlo et al, Tetrahedron Letters, vol. 31, No. 22, pp. 3101-3104 (1990).
"Zur Spaltung von 2,3'-Anhydronucleosiden mit Halogen-wasserstoffsauren", Zeitschrift fur Chemie, vol. 23, 335 (1983).
V. G. Kowollik et al., "Ein neuer Zugang zu 1-(2,3-Didesoxy-3-fluor-.beta.-D-ribofuranosyl)-pyrimidinen", Journal fur Praktische Chemie, vol. 315, 895 (1973).
V. G. Kowollik et al., "Cleavage of a 2,3'-Anhydro Ring by Hydrogen Fluoride", Nucleic Acid Chemistry, Part I, pp. 299-302 (1978).

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