Probing of PSE acetal protection for nucleoside chemistry

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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. © 2007 Elsevier Ltd. All rights reserved.

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Uttaro, J. P., Uttaro, L., Tatibouet, A., Rollin, P., Mathé, C., & Périgaud, C. (2007). Probing of PSE acetal protection for nucleoside chemistry. Tetrahedron Letters, 48(22), 3851–3854. https://doi.org/10.1016/j.tetlet.2007.03.153

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