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Synthesis and Conformational Study of 2-Trityloxymethyltet­rahydrofurans as Key Intermediates for Antiviral Nucleosides

Choi Hye-Young    (College of Pharmacy, Sookmyung Women's University   ); Kim Hee-Doo    (College of Pharmacy, Sookmyung Women's University  );
  • 초록

    We wanted to elucidate the reason why the trityloxymethyl substituent in $\gamma$ -trityloxymethyl- $\gamma$ ­butyrolactone takes a sterically unfavorable specific conformation, and so we synthesized 5-trityloxymethyldihydrofuran-3-one, 3-(trityloxymethyl)-4-butanolide and 2-trityloxymethyl- tetrahy­drofuran and we then analyzed their conformation by $^{1}H-NMR$ analysis.


  • 주제어

    Conformational analysis .   Vicinal coupling constant .   Gauche effect .   Electrostatic interaction .   Antiviral nucleoside.  

  • 참고문헌 (9)

    1. Agrofolio, I. A. and Challand, S. R., Acyclic Carbocyclic and LNucleosides. Kluwer Academic Publisher: Dordrecht. Boston, Lodon, 1998 
    2. Haasnoot, C. A. G., De Leeuw, F. A. A. M., and Altona, C., The relationship between proton-proton NMR coupling constants and substituent electronegativities-1. Tetrahedron, 36, 2783- 2792 (1980) 
    3. Tomioka, K., Kawasaki, H., Iitaka, Y., and Koga, K., Enantiospecific total synthesis of (-)-megaphone by a highly controlled consecutive 1,4- and 1,3-asymmetric induction. Tetrahedron Lett., 26, 903-906 (1985) 
    4. Tomioka, K., Cho, Y.-S., Sato, F., and Koga, K., Stereoselective reaction 14. Efficient Enantioselective construction of quaternary carbon center by sequential dialkylation of (S)-${\gamma}$-[(Trityloxy)methyl]-$\gamma$-butyrolactone. Synthesis of optically active ${\beta}$,${\beta}$-disubstituted ${\gamma}$-lactones. J. Org. Chem., 53, 4094-4098 (1988). 
    5. Coppola, G. M. and Schuster, H. F., Asymmetric Synthesis: Construction of chiral molecules using amino acids. John Wiley & Sons, Inc., New York, 1987 
    6. Takano, S., Yonaga, M., and Ogasawara, K., Synthesis of both enantiomers of ${\gamma}$-(trityloxymethyl)-${\gamma}$-butyrolactone from a single progenitor, (S)-(+)-glutamic acid. Synthesis, 4, 265- 266 (1981) 
    7. Wolfe, S., Gauche effect. Stereochemical consequences of adjacent electron pairs and polar bonds. Acc. Chem. Res., 5, 102-111 (1972) 
    8. Morimoto, Y. and Shirahama, H., Unexpected stability of ${\gamma}$- lactone with axial substituents rather than equatorial ones. Conformational evaluation by molecular mechanics and molecular orbital calculations. Tetrahedron, 53, 2013-2024 (1997) 
    9. Tomioka, K., Kawasaki, H., and Koga, K., Control elements in the asymmetric tandem alkylation of ${\alpha}$-alkylidene-${\gamma}$-butyrolactone derivatives. Tetrahedron Lett., 26, 3027-3030 (1985) 

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