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Fluoride Ion Catalyzed Alkylation of Nucleic Acid Derivatives Using Trialkyl Phosphates, Dialkyl Sulfates and Alkyl Methanesulfonates

Fluoride Ion Catalyzed Alkylation of Nucleic Acid Derivatives Using Trialkyl Phosphates, Dialkyl Sulfates and Alkyl Methanesulfonates

K K Ogilvie, S L Beaucage, M F Gillen, D W Entwistle

Nucleic Acids Res. 1979;6(6):2261-73.

PMID: 223127

Abstract:

Trimethyl phosphate, dimethyl and diethyl sulfate and methyl and ethyl methanesulfonate all give high yields of alkylation on purines and pyrimidines in the presence of tetrabutylammonium fluoride. Trimethyl phosphate produces near quantitative yields of diesters of nucleic acids but gives virtually no triester formation. The alkyl sulfates produce very high yields of triesters of nucleic acids including cyclic phosphates while the alkyl methanesulfonates are intermediate in reactivity. It was observed that in the absence of fluoride ion the dialkylsulfates gave reasonable yields of thymidine monosulfates.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP65411496	Tetrabutylammonium methanesulfonate		65411-49-6	Price

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