Photoredox-Catalyzed Deformylative 1,4-Addition of 2 '-Deoxy-5 '-O-phthalimidonucleosides for Synthesis of 5 '-Carba Analogs of Nucleoside 5 '-Phosphates

A concise approach for the synthesis of the 5'-carba analogs of nucleoside 5'-phosphates from 2'-deoxy-5'-O-phthalimidonucleosides by a visible light-mediated deformylative 1,4-addition was developed. This method enabled rapid and facile generation of 4'-carbon radicals of n...

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Published inJournal of organic chemistry Vol. 83; no. 18; pp. 10701 - 10708
Main Authors Ito, Yuta, Kimura, Airi, Osawa, Takashi, Hari, Yoshiyuki
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 21.09.2018
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PHOSPHATE
HEPATITIS-C VIRUS
CHAIN TERMINATORS
ACIDS
PHOSPHONATE PRODRUGS
ANTIVIRAL ACTIVITY
HCV
POTENTIAL INHIBITORS
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Summary:A concise approach for the synthesis of the 5'-carba analogs of nucleoside 5'-phosphates from 2'-deoxy-5'-O-phthalimidonucleosides by a visible light-mediated deformylative 1,4-addition was developed. This method enabled rapid and facile generation of 4'-carbon radicals of nucleosides. Moreover, this synthetic strategy was applicable to the 5'-carba analogs of nucleoside 5'-phosphates as well as other 5'-carba nucleosides bearing methoxycarbonyl, cyano, and N-methylsulfamoyl groups.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b00637