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Asymmetric Synthesis of Novel Thioiso Dideoxynucleosides with Exocyclic Methylene as Potential Antiviral Agents

Title
Asymmetric Synthesis of Novel Thioiso Dideoxynucleosides with Exocyclic Methylene as Potential Antiviral Agents
Authors
Gunaga P.Baba M.Jeong L.S.
Ewha Authors
정낙신
Issue Date
2004
Journal Title
Journal of Organic Chemistry
ISSN
0022-3263JCR Link
Citation
Journal of Organic Chemistry vol. 69, no. 9, pp. 3208 - 3211
Indexed
SCIE; SCOPUS WOS scopus
Document Type
Article
Abstract
Novel thioiso pyrimidine and purine nucleosides substituted with exocyclic methylene have been synthesized, starting from D-xylose. The glycosyl donor 14 was synthesized from D-xylose, using cyclization of dimesylate 10 with sodium sulfide as a key step. Cyclization proceeded in pure SN2 reaction without going through SN1 reaction in the presence of an allylic functional group at low reaction temperature (0 °C) in polar solvent (DMF), affording compound 12 as a major product. At higher temperatures, S N2′ product 11 was almost exclusively obtained as a major product. On the other hand, glycosylation of 14 with 6-chloropurine under Mitsunobu conditions afforded the desired SN2 product 26, while palladium-catalyzed glycosylation resulted in the sole formation of S N2′ product 34.
DOI
10.1021/jo035735b
Appears in Collections:
약학대학 > 약학과 > Journal papers
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