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Synthesis of conformationally locked methanocarba-uridine as a precursor for nucleotides agonizing P2Y6 receptor

Title
Synthesis of conformationally locked methanocarba-uridine as a precursor for nucleotides agonizing P2Y6 receptor
Authors
Kim S.-A.Hyun M.L.Ryu J.-S.Hak S.K.
Ewha Authors
류재상
SCOPUS Author ID
류재상scopus
Issue Date
2007
Journal Title
Synlett
ISSN
0936-5214JCR Link
Citation
no. 7, pp. 1055 - 1058
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
Conformationally locked uridine in the 'southern' conformation, which could be an important precursor for corresponding nucleotides, was stereoselectively synthesized. Southern uridine nucleotides are expected to be full agonists for the P2Y6 receptor. Poor diastereoselectivity in the osmium-mediated dihydroxylation on the allyl amine was overcome by introduction of an allyl azide on which osmium medium hydroxylation, and subsequent cyclization yielded 6-oxabicyclo[3.2.0]heptane in a 9:1 ratio. High regioselectivity between the 2′- and 3′-hydroxyl groups in the intramolecular O-alkylation and construction of uracil moiety from the azido group provided the final target, a southern 2′-benzoylated uridine derivative. © Georg Thieme Verlag Stuttgart.
DOI
10.1055/s-2007-973902
Appears in Collections:
약학대학 > 약학과 > Journal papers
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