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Synlett 2007(7): 1055-1058  
DOI: 10.1055/s-2007-973902
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Conformationally Locked Methanocarba-uridine as a Precursor for Nucleotides Agonizing P2Y6 Receptor

Soon-Ai Kima, Hyun Min Leea, Jae-Sang Ryub, Hak Sung Kim*a
a College of Pharmacy, Wonkwang University, 344-2 Shinyong-Dong, Iksan, Jeonbuk 570-749, South Korea
Fax: +82(63)8431581; e-Mail: hankidad@wku.ac.kr;
b College of Pharmacy, Ewha Womans University, Seoul 120-750, South Korea
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Publication History

Received 4 January 2007
Publication Date:
13 April 2007 (online)

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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.

Key words

nucleoside - nucleotide - carbohydrate - carbocycle - stereoselective synthesis

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