Probing of PSE acetal protection for nucleoside chemistry

The use of phenylsulfonylethylidene (PSE) acetal as a protective group in nucleoside chemistry is reported. 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...

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Bibliographic Details
Published in:Tetrahedron letters 2007-05, Vol.48 (22), p.3851-3854
Main Authors: Uttaro, Jean-Pierre, Uttaro, Lycia, Tatibouet, Arnaud, Rollin, Patrick, Mathé, Christophe, Périgaud, Christian
Format: Article
Language:English
Subjects:
Biochemistry
Biochemistry, Molecular Biology
Life Sciences
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Summary:The use of phenylsulfonylethylidene (PSE) acetal as a protective group in nucleoside chemistry is reported. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.03.153