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Regioselective O 2′, O 3′‐Deacetylations of Peracetylated Ribonucleosides by Using Tetra‐ n ‐butylammonium Fluoride
Author(s) -
Babu Kumar Arun,
Manetsch Roman
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201400085
Subject(s) - chemistry , regioselectivity , acetylation , tetra , fluoride , combinatorial chemistry , deoxyribonucleosides , organic chemistry , medicinal chemistry , catalysis , enzyme , inorganic chemistry , biochemistry , gene
A robust, mild, and highly regioselective deacetylation of 1,2‐diol diacetates in the presence of other acetate functions was achieved by using tetra‐ n ‐butylammonium fluoride. This method provided a single‐step route to access O 5′‐acetyl ribonucleosides, a key intermediate in the synthesis of biomedically important nucleosides and nucleotides. Moreover, it offered the general applicability of a non‐enzymatic method for the selective deacetylation of peracetylated 2′‐deoxyribonucleosides. Its synthetic utility was further demonstrated by the synthesis of molecules of biomedical interest by using this particular deacetylation reaction.