Probing of PSE acetal protection for nucleoside chemistry |
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| Authors: | Jean-Pierre Uttaro Arnaud Tatibouet Christophe Mathé |
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| Institution: | a Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS—UM1—UM2, Université Montpellier 2, Case Courrier 1705, Place E. Bataillon, 34095 Montpellier Cedex 05, France
b Institut de Chimie Organique et Analytique, UMR 6005, Université d’Orléans, B.P. 6759, 45067 Orléans, France |
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| Abstract: | The use of phenylsulfonylethylidene (PSE) acetal as a new 3′,5′-bridged protecting group in nucleoside chemistry is reported. The PSE acetal demonstrates to be compatible with Lewis acids used in standard glycosylation reactions. In addition, a selective 2′-O-deacylation from a 3′,5′-O-(phenylsulfonyl)-2′-O-acetyl nucleoside can be achieved, giving access to subsequent chemical modifications in 2′ position. However, the PSE acetal cleavage surprisingly appeared to be purine/pyrimidine base dependent. |
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