ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Stereospecific Synthesis of the Anticancer Agent 5′-Deoxy-5-fluorouridine and its 5′-deuteriated Derivatives5′-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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19820650525
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