Bulletin of the Korean Chemical Society

  • 제19권11호
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  • Pages.1239-1244
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  • 1998
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Syntheses of Mannosidic Disaccharides from Derivatives of Ethylthio $\alpha$-D-Mannopyranoside

  • 발행 : 1998.11.20
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초록

Derivatives of ethylthio α-D-mannopyranoside as glycosyl donors are compared in coupling efficiency and stercoselectivity with varying thiophilic promoters from methyl triflate (MeOTf), dimethyl(methylthio)sulfonium triflate (DMTST) to iodonium dicollidine perchlorate (IDCP), solvents and glycosyl acceptors. IDCP was the most efficient promoter in coupling of perbenzylated ethylthio-α-D-mannopyranosides (1 and 2), giving α-Dmannosyl disaccharides preferentially, whereas inactive in coupling of 4,6-O-benzylidene derivatives 3 and 4. MeOTf and DMTST promoted coupling of 4,6-O-benzylidene derivatives 3 and 4, but P-D-mannopyranosyl disaccharides were formed preferentially. Coupling reaction was retarded as solvent polarity decreased.

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참고문헌

  1. J. Am. Chem. Soc. v.117 Danishefsky, S. J.;Behar, V.;Randolph, J. T.;Lloyd, K. O.
  2. Tetrahedron lett. v.30 Yamazaki, F.;Nukada, T.;Ogawa, T.
  3. Tetrahedron lett. v.27 Ogawa, T.;Sugimoto, M.;Kitajima, T.;Sadazai, K. K.;Nukada, T.
  4. Carbohydr. Res. v.216 Chernyak, A. Y.;Kononov, L. O.;Kochetkov, N. K.
  5. Carbohydr. Res. v.280 Nakahara, Y.;Shibayama, S.;Nakahara, Y.;Ogawa, T.
  6. Carbohydr. Res. v.110 Dmitriev, B. A.;Nikolaev, A. V.;Shashkov, A. S.;Kochetkov, N. K.
  7. Carbohydr. Res. v.131 Jnsson, P. E.;Lindberg, B.;Lonngren, J.;Ortega, C.
  8. Carbohydr. Res. v.145 Jnsson, P. E.;Lonngren, J.;Widmalm, G.
  9. Carbohydr. Res. v.104 Ogawa, T.;Yanmamoto, H.
  10. Carbohydr. Res. v.157 Sadozai, K. K.;Nukada, T.;Ito Y.;Nakahara, Y.;Ogawa, T.
  11. Carbohydr. Res. v.84 Betaneli, V. I.;Ovchinnikov, M. V.;Backinowsky, L. V.;Kochetkov, N. K.
  12. Carbohydr. Res. v.278 Khan S. H.;Matta K. L.
  13. Carbohydr. Res. v.119 Garegg, P. J.;Henrichson, C.;Norberg, T.;Ossowski, P.
  14. Carbohydr. Res. v.37 Bebault, G. M.;Dutton, G. S.D.
  15. J. Am. Chem. Soc. v.113 Barresi, F.;Hindsgaul, O.
  16. Synlett Barresi, F.;Hindsgaul, O.
  17. Chem. Rev. v.93 Toshima, K.;Tatsrta, K.
  18. Tetrahedron Lett. v.31 Veeneman, G. H.;van Boom, J. H.
  19. J. Am. Chem. Soc. v.110 Mootoo, D. R.;Konradsson, P.;Udodong, U.;Fraser-Reid, B.
  20. Tetrahedron Lett. v.31 Konradsson, P.;Udodong, U. E.;Fraser-Reid, B.
  21. J. Carbohydr. Chem. v.14 Hotta, K.;Itoh, K.;Kameyama, A.;Ishida, H.;Kiso, M.;Hasegawa, A.
  22. Tetrahedron Lett. v.31 Veeneman, G. H.;van Leeuwen, S.H.;van Boom, J. H.
  23. Carbohydr. Res. v.232 Houdier, S.;Vottero, P. J. A.
  24. Carbohydr. Res. v.139 Lonn, H.
  25. Carbohydr. Res. v.254 Oscarson, S.;Ritzen, H.
  26. J. Chem. Soc. Perkin Trans. v.II Ravenscroft, M.;Roberts, R. M. G.;Tillett, J. G.
  27. Synlett Demchenko, A.;Stauch, T.;Boons, G.-J.
  28. Can. J. Chem. v.43 Lemieux, R. U.;Morgan, A. R.
  29. Ph. D. Thesis Yoon, S.;Shin, J. E. N.
  30. J. Org. Chem. v.61 Crich, D.;Sun, S.
  31. J. Org. Chem. v.62 Crich, D.;Sun, S.
  32. J. Org. Chem. v.46 Srivastava V. K.;Schuerch C.
  33. Carbohydr. Res. v.79 Srivastava V. K.;Schuerch C.
  34. J. Am. Chem. Soc. v.114 Stork, G.;Kim, G.
  35. Can. J. Chem. v.64 Tahir, S. H.;Hindsgaul, O.
  36. Synth. commun. v.26 Misra, A. K.;Basu, S.;Roy, N.
  37. Tetrahedron Lett. v.56 Dan, A.;Itom Y.;Ogawa, T.
  38. Carbohydrate Chemistry Kennedy, J. F.
  39. J. Am. Chem. Soc. v.118 Stork, G.;La Clair, J. J.
  40. The 13th IUPAC Conference on Physical Organic Chemistry v.P119 Yun, M.;Shin, Y.;Chun, K. H.;Shin, J. E. N.
  41. J. Am. Chem. Soc. v.120 Crich, D.;Sun, S.