Synthesis of 2′,3′-Dideoxyinosine via Radical Deoxygenation

A synthetic method for 2 ′,3 ′-dideoxyinosine (ddI) from inosine was established via radical deoxygenation of N1,5 ′-O-diprotected-2 ′,3 ′-bis-S-methyl dithiocarbonate of inosine derivatives. The radical deoxygenation proceeded smoothly to give the desired dideoxy compounds in good yields using 1-et...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2007-01, Vol.26 (8-9), p.985-988
Main Authors: Torii, Takayoshi, Izawa, Kunisuke, Cho, Dae Hyan, Jang, Doo Ok
Format: Article
Language:English
Subjects:
1-ethylpiperidinium hypophosphite
2′,3′-Dideoxyinosine
debenzylation
Didanosine - chemical synthesis
Didanosine - chemistry
Free Radicals - chemistry
Methods
N1 and 5′-O-protection
Oxidation-Reduction
radical deoxygenation
Reverse Transcriptase Inhibitors - chemical synthesis
Reverse Transcriptase Inhibitors - chemistry
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Summary:A synthetic method for 2 ′,3 ′-dideoxyinosine (ddI) from inosine was established via radical deoxygenation of N1,5 ′-O-diprotected-2 ′,3 ′-bis-S-methyl dithiocarbonate of inosine derivatives. The radical deoxygenation proceeded smoothly to give the desired dideoxy compounds in good yields using 1-ethylpiperidinium hypophosphite and triethylborane. Benzyl or p-methoxybenzyl protection of inosine at the N1, 5 ′-O-positions were effective for the ddI synthesis.
ISSN:1525-7770
1532-2335
DOI:10.1080/15257770701508414