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Synthesis of a 3′‐Deoxy‐ C ‐Nucleoside Phosphonate Bearing 9‐Deazaadenine as Base Moiety
Author(s) -
Nie Peng,
Groaz Elisabetta,
De Jonghe Steven,
Andrei Graciela,
Herdewijn Piet
Publication year - 2018
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.201800889
Subject(s) - chemistry , phosphonate , moiety , anomer , stereochemistry , nucleoside , epimer , glycosylation , prodrug , stereoselectivity , organic chemistry , catalysis , biochemistry
Herein, the synthesis of the first example of a 3′‐deoxy‐5′‐phosphonate 2′[R] C‐nucleoside and its corresponding prodrug is presented. The developed route involves a reductive debromination at the 2′‐position of a suitably substituted 9‐deazaadenosine intermediate, followed by a stereoselective glycosylation at the 5′‐anomeric position to achieve the installation of the phosphonomethoxy functionality. The target compound with the desired configuration is formed upon base‐promoted epimerization at the 2′[S]‐position of the sugar moiety.