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1. Regiospecific synthesis of 6-halouridine derivatives: An effective method for coupling sterically hindered pyrimidine bases to ribose

Author

Daniel J. Blackburn, Weiming Wu, and Greggory T. Kent

Subjects
Steric effects, Trimethylsilyl, Pyrimidine, 010405 organic chemistry, Chemistry, Organic Chemistry, 010402 general chemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, 0104 chemical sciences, Lewis acid catalysis, chemistry.chemical_compound, Trimethylsilyl trifluoromethanesulfonate, Reagent, Drug Discovery, Ribose, Organic chemistry, Acetamide
Abstract

6-Halouridine derivatives were synthesized regiospecifically through the coupling of N3-protected 6-halouracil to a ribose derivative. The combination of the silylating reagent N,O -bis(trimethylsilyl)acetamide and Lewis acid catalyst trimethylsilyl trifluoromethanesulfonate is unique in their ability to facilitate the coupling of sterically hindered pyrimidine bases to ribose to form nucleoside derivatives.

Published
2017
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