Synthesis of a C-Nucleoside Phosphonate by Base-Promoted Epimerization | Zendy

Peng Nie | Zendy; Elisabetta Groaz | Zendy; Steven De Jonghe | Zendy; Eveline Lescrinier | Zendy; Piet Herdewijn | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Synthesis of a C-Nucleoside Phosphonate by Base-Promoted Epimerization

Author(s) -

Peng Nie,

Elisabetta Groaz,

Steven De Jonghe,

Eveline Lescrinier,

Piet Herdewijn

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b00123

Subject(s) - chemistry , epimer , phosphonate , nucleoside , base (topology) , stereochemistry , nucleic acid , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry , mathematical analysis , mathematics

The efficient synthesis of a [2'S] C-nucleoside phosphonate and its corresponding prodrug has been realized. A phosphonomethoxy group was stereoselectively introduced at the anomeric 5'-carbon atom through glycosylation of a benzoyl protected [5'R]-acetoxy-[2'R]-9-deazaadenine. An unexpected epimerization at the 2'-position of the sugar moiety occurred upon removal of the protecting groups, but this was further exploited as a key reaction for improved synthesis of the target compound.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research