Journal
TETRAHEDRON LETTERS
Volume 54, Issue 30, Pages 3949-3952Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.05.062
Keywords
Nucleoside; Nucleoside phosphonate; Nucleotide; Glycosylation; Antiviral
Categories
Funding
- JSPS [24590143]
- Ministry of Education, Culture, Sport, Science, and Technology, Japan (MEXT)
- Grants-in-Aid for Scientific Research [24590143] Funding Source: KAKEN
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The synthesis of a novel nucleoside phosphonate constructed on a branched-threo-tetrofuranose scaffold, as a potential antiviral agent, is described. The pseudosugar moiety served as the nucleoside skeleton was produced starting from 2-butyne-1,4-diol in 10-steps. Glycosylation with the pseudosugar involved stereoselective neighboring group participation of p-anisyl group and gave the nucleoside derivative in 94% yield. After manipulating the protecting group and introduction of a methylenephosphate unit, the synthesis of the target novel cytidine phosphonate was achieved. The resulting nucleoside, a synthetic intermediate of the nucleoside phosphonate, would also be expected to serve as a useful building block for the synthesis of novel antisense/antigene derivatives. (C) 2013 Elsevier Ltd. All rights reserved.
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