Probing of PSE acetal protection for nucleoside chemistry
| Autor: | Patrick Rollin, Lycia Uttaro, Arnaud Tatibouët, Jean-Pierre Uttaro, Christophe Mathé, Christian Périgaud |
|---|---|
| Přispěvatelé: | Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM) |
| Jazyk: | angličtina |
| Rok vydání: | 2007 |
| Předmět: |
Purine
Glycosylation Pyrimidine 010405 organic chemistry Stereochemistry Organic Chemistry Acetal biochemical phenomena metabolism and nutrition 010402 general chemistry Cleavage (embryo) 01 natural sciences Biochemistry 0104 chemical sciences chemistry.chemical_compound chemistry Drug Discovery polycyclic compounds Lewis acids and bases [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry Molecular Biology/Biochemistry [q-bio.BM] Protecting group Nucleoside |
| Zdroj: | Tetrahedron Letters Tetrahedron Letters, Elsevier, 2007, 48, pp.3851-3854. ⟨10.1016/j.tetlet.2007.03.153⟩ |
| ISSN: | 0040-4039 |
| DOI: | 10.1016/j.tetlet.2007.03.153⟩ |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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