Studies on the Synthesis of N′-Acetyl AZA-Analogues of Ganciclovir—Unexpected Liability of N′-(2-Hydroxyethyl)-Azanucleosides Under Basic Conditions

M Koszytkowska-Stawińska

Index: Koszytkowska-Stawinska, Mariola Nucleosides, Nucleotides and Nucleic Acids, 2010 , vol. 29, # 10 p. 768 - 785

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Abstract

The O′-pivaloyl diesters of N′-acetyl-azanucleosides were obtained from N-[1, 3-di (pivaloyloxy) prop-2-yl]-N-(pivaloyloxymethyl) acetamide and a silylated nucleobase under Vorbrüggen's conditions. Unexpectedly, de-pivaloylation of the diesters under basic conditions afforded the corresponding nucleobase and N-acetylserinol. Mechanistic investigations showed that these products result from the following cascade of ...