1. Preparation of a Fludarabine Intermediate via Selective Alkylation of 2-Fluoroadenine.
- Author
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Schulmeier, BrianE., Cantrell, WilliamR., and Bauta, WilliamE.
- Subjects
- *
SOLVENTS , *ALKALI metals , *FLUIDS , *SOLUTION (Chemistry) , *CHEMISTRY - Abstract
The reaction between 2-fluoroadenine ( 3 ) and 1,3,5-tri- O -benzyl-1- α -d-chloroarabinofuranose ( 4 ) with potassium t- amylate was evaluated in various solvents to afford 9- β -d-(2,3,5-tri- O -benzyl-arabinofuranosyl)-2-fluoroadenine ( 5 ) and the corresponding α -anomer ( 6 ). In addition, 7- β -d-(2,3,5-tri- O -benzyl-arabinofuranosyl)-2-fluoroadenine ( 7 ) and an unusual “ bis -fluoroadenine” nucleoside ( 8 ) were isolated as by-products. The highest anomeric ratio (β/α > 10) and conversion (>80%) were observed with the highly polar solvent sulfolane. This reaction was demonstrated on gram scale as a practical laboratory synthesis of 5 , a known intermediate in the synthesis of fludarabine. [ABSTRACT FROM AUTHOR]
- Published
- 2006
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