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Stereospezifische Synthese des Cancerostatikums 5′‐Desoxy‐5‐fluor‐uridin (5‐DFUR) und seiner 5′ ‐deuterierten Derivate
Author(s) -
Kiss Joseph,
D'Souza Richard,
Van Koeveringe Jan A.,
Arnold Wolf
Publication year - 1982
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19820650525
Subject(s) - chemistry , trimethylsilyl trifluoromethanesulfonate , anomer , stereospecificity , stereochemistry , nucleoside , trifluoromethanesulfonate , epimer , trimethylsilyl , yield (engineering) , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
Stereospecific Synthesis of the Anticancer Agent 5′‐Deoxy‐5‐fluorouridine and its 5′‐deuteriated Derivatives 5′‐Deoxy‐5‐fluorouridine (5′‐DFUR) has been obtained in high yield and purity by Stereospecific condensation of the anomeric 5¨deoxy‐1,2,3‐tri‐ O ‐acetyl‐D‐ribofu‐ranose with bis(trimethylsilylated)‐5‐fluorouracil in the presence of trimethylsilyl trifluoromethanesulfonate, and by subsequent cleavage of the acetate protecting groups. A minor by‐product of the synthesis, the α‐anomeric nucleoside is produced by a (β‐α)‐epimerization, a procedure which is catalyzed by trimethylsilyl trifluoromethanesulfonate. The corresponding 5′‐deuteriated, and 5′,5′‐dideuteriated nucleosides have also been synthesized using an analogous way. The synthesis of the sugar components of the latter nucleosides ‐ starting from D‐ribose, D‐xylose and D‐glucose ‐is also described.