메뉴 건너뛰기




Volumn 4, Issue 11, 1998, Pages 2182-2190

p-Methoxybenzylidene-tethered β-mannosylation for stereoselective synthesis of asparagine-linked glycan chains

Author keywords

Glycosides; Intramolecular aglycon delivery; Oligosaccharides; Saccharide chemistry; Stereoselectivity

Indexed keywords

ASPARAGINE LINKED OLIGOSACCHARIDE; GLYCOPROTEIN; GLYCOSIDE; OLIGOSACCHARIDE;

EID: 0031772091     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(19981102)4:11<2182::aid-chem2182>3.0.co;2-u     Document Type: Article
Times cited : (68)

References (70)
  • 2
    • 0027318961 scopus 로고
    • T.W. Rademacher, R.B. Parekh, R. A. Dwek, Ann. Rev. Biochem. 1988, 57, 785; A. Varki, Glycobiology 1993, 3, 97.
    • (1993) Glycobiology , vol.3 , pp. 97
    • Varki, A.1
  • 7
    • 0030894278 scopus 로고    scopus 로고
    • and references therein
    • D. Crich, S. Sun, J. Org. Chem. 1997, 62, 1198, and references therein.
    • (1997) J. Org. Chem. , vol.62 , pp. 1198
    • Crich, D.1    Sun, S.2
  • 18
    • 85022429859 scopus 로고
    • F. Barresi, O. Hindsgaul, J. Am. Chem. Soc. 1991, 113, 9376; F. Barresi, O. Hindsgaul, Synlett 1992, 759.
    • (1992) Synlett , pp. 759
    • Barresi, F.1    Hindsgaul, O.2
  • 19
    • 84921177645 scopus 로고
    • G. Stork, G. Kim, J. Am. Chem. Soc. 1992, 114, 1087; G. Stork, J. J. La Clair, J. Am. Chem. Soc. 1996, 118, 247.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 1087
    • Stork, G.1    Kim, G.2
  • 21
    • 0001325832 scopus 로고
    • a) Y. Ito, T. Ogawa, Angew. Chem. 1994, 106, 1843; Angew. Chem. Int. Ed. Engl. 1994, 33, 1765;
    • (1994) Angew. Chem. , vol.106 , pp. 1843
    • Ito, Y.1    Ogawa, T.2
  • 22
    • 26844498306 scopus 로고
    • a) Y. Ito, T. Ogawa, Angew. Chem. 1994, 106, 1843; Angew. Chem. Int. Ed. Engl. 1994, 33, 1765;
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1765
  • 27
    • 0004148597 scopus 로고
    • (Eds.: M. Fukuda, O. Hindsgaul) IRL, Oxford
    • M. Fukuda, in Molecular Glycobiology (Eds.: M. Fukuda, O. Hindsgaul) IRL, Oxford, 1994. p. 1.
    • (1994) Molecular Glycobiology , pp. 1
    • Fukuda, M.1
  • 29
    • 0027296563 scopus 로고
    • For example: K. Yamashita, K. Totani, Y. Iwaki, I. Takamizawa, N. Tateishi, T. Higasi, Y. Sakamoto, A. Kobata, J. Biochem. (Tokyo) 1989, 105, 728; K. Yamashita, K. Taketa, S. Nishi, K. Fukushima, Cancer Res. 1993, 53, 2970.
    • (1993) Cancer Res. , vol.53 , pp. 2970
    • Yamashita, K.1    Taketa, K.2    Nishi, S.3    Fukushima, K.4
  • 30
    • 0000159086 scopus 로고
    • For general discussion, see: H. Paulsen, Angew. Chem. 1982, 94, 184; Angew. Chem. Int. Ed. Engl. 1982, 21, 155.
    • (1982) Angew. Chem. , vol.94 , pp. 184
    • Paulsen, H.1
  • 31
    • 0040657616 scopus 로고
    • For general discussion, see: H. Paulsen, Angew. Chem, 1982, 94, 184; Angew. Chem. Int. Ed. Engl. 1982, 21, 155.
    • (1982) Angew. Chem. Int. Ed. Engl. , vol.21 , pp. 155
  • 40
    • 3743067260 scopus 로고    scopus 로고
    • When the purification by size-exclusion column chromatography was omitted at the stage of the mixed acetal 12, disaccharide 11 with identical quality was obtained in 51% overall yield based upon 10
    • When the purification by size-exclusion column chromatography was omitted at the stage of the mixed acetal 12, disaccharide 11 with identical quality was obtained in 51% overall yield based upon 10.
  • 41
    • 3743070615 scopus 로고    scopus 로고
    • unpublished results
    • S configuration does not seem to be a critical factor for successful intramolecular aglycon delivery. Detailed discussion will be reported in due course. (M. Lergenmüller, T. Nukada, K. Kuramochi, A. Dan, T. Ogawa, Y. Ito, unpublished results)
    • Lergenmüller, M.1    Nukada, T.2    Kuramochi, K.3    Dan, A.4    Ogawa, T.5    Ito, Y.6
  • 55
    • 0001354297 scopus 로고
    • C. Unverzagt, Angew. Chem. 1994, 106, 1170; Angew. Chem. Int. Ed. Engl. 1994, 33, 1102; J. Seifert, C. Unverzagt, Tetrahedron Lett. 1996, 37, 6527; C. Unverzagt, Angew. Chem. 1996, 108, 2507; Angew. Chem. Int. Ed. Engl. 1996, 35, 2350.
    • (1994) Angew. Chem. , vol.106 , pp. 1170
    • Unverzagt, C.1
  • 56
    • 33748242969 scopus 로고
    • C. Unverzagt, Angew. Chem. 1994, 106, 1170; Angew. Chem. Int. Ed. Engl. 1994, 33, 1102; J. Seifert, C. Unverzagt, Tetrahedron Lett. 1996, 37, 6527; C. Unverzagt, Angew. Chem. 1996, 108, 2507; Angew. Chem. Int. Ed. Engl. 1996, 35, 2350.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 1102
  • 57
    • 0030565553 scopus 로고    scopus 로고
    • C. Unverzagt, Angew. Chem. 1994, 106, 1170; Angew. Chem. Int. Ed. Engl. 1994, 33, 1102; J. Seifert, C. Unverzagt, Tetrahedron Lett. 1996, 37, 6527; C. Unverzagt, Angew. Chem. 1996, 108, 2507; Angew. Chem. Int. Ed. Engl. 1996, 35, 2350.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6527
    • Seifert, J.1    Unverzagt, C.2
  • 58
    • 0000713501 scopus 로고    scopus 로고
    • C. Unverzagt, Angew. Chem. 1994, 106, 1170; Angew. Chem. Int. Ed. Engl. 1994, 33, 1102; J. Seifert, C. Unverzagt, Tetrahedron Lett. 1996, 37, 6527; C. Unverzagt, Angew. Chem. 1996, 108, 2507; Angew. Chem. Int. Ed. Engl. 1996, 35, 2350.
    • (1996) Angew. Chem. , vol.108 , pp. 2507
    • Unverzagt, C.1
  • 59
    • 0030445043 scopus 로고    scopus 로고
    • C. Unverzagt, Angew. Chem. 1994, 106, 1170; Angew. Chem. Int. Ed. Engl. 1994, 33, 1102; J. Seifert, C. Unverzagt, Tetrahedron Lett. 1996, 37, 6527; C. Unverzagt, Angew. Chem. 1996, 108, 2507; Angew. Chem. Int. Ed. Engl. 1996, 35, 2350.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2350
  • 60
    • 0342352088 scopus 로고
    • W. Gunther, H. Kunz, Angew. Chem. 1990, 102, 1068; Angew. Chem. Int. Ed. Engl. 1990, 29, 1050.
    • (1990) Angew. Chem. , vol.102 , pp. 1068
    • Gunther, W.1    Kunz, H.2
  • 61
    • 0025074795 scopus 로고
    • W. Gunther, H. Kunz, Angew. Chem. 1990, 102, 1068; Angew. Chem. Int. Ed. Engl. 1990, 29, 1050.
    • (1990) Angew. Chem. Int. Ed. Engl. , vol.29 , pp. 1050
  • 62
    • 33749479027 scopus 로고
    • Y. Ito, T. Ogawa, M. Numata, M. Sugimoto, J. Am. Chem. Soc. 1988; A. Hasegawa, T. Nagahama, H. Ohki, K. Hotta, H. Ishida, M. Kiso, J. Carbohydr. Chem. 1991, 10, 493; A. Hasegawa, H. Ohki, T. Nagahama, H. Ishida, M. Kiso, Carbohydr. Res. 1991, 212, 277; T. J. Martin, R. R. Schmidt, Tetrahedron Lett. 1992, 33, 6123; A. V. Demchenko, G.-J. Boons, Tetrahedron Lett. 1998, 39, 3065; J. C. Castro-Palomino, Y. E. Tsvetkov, R. R. Schmidt, J. Am Chem. Soc. 1998, 120, 5434.
    • (1988) J. Am. Chem. Soc.
    • Ito, Y.1    Ogawa, T.2    Numata, M.3    Sugimoto, M.4
  • 63
    • 33749479027 scopus 로고
    • Y. Ito, T. Ogawa, M. Numata, M. Sugimoto, J. Am. Chem. Soc. 1988; A. Hasegawa, T. Nagahama, H. Ohki, K. Hotta, H. Ishida, M. Kiso, J. Carbohydr. Chem. 1991, 10, 493; A. Hasegawa, H. Ohki, T. Nagahama, H. Ishida, M. Kiso, Carbohydr. Res. 1991, 212, 277; T. J. Martin, R. R. Schmidt, Tetrahedron Lett. 1992, 33, 6123; A. V. Demchenko, G.-J. Boons, Tetrahedron Lett. 1998, 39, 3065; J. C. Castro-Palomino, Y. E. Tsvetkov, R. R. Schmidt, J. Am Chem. Soc. 1998, 120, 5434.
    • (1991) J. Carbohydr. Chem. , vol.10 , pp. 493
    • Hasegawa, A.1    Nagahama, T.2    Ohki, H.3    Hotta, K.4    Ishida, H.5    Kiso, M.6
  • 64
    • 0026173653 scopus 로고
    • Y. Ito, T. Ogawa, M. Numata, M. Sugimoto, J. Am. Chem. Soc. 1988; A. Hasegawa, T. Nagahama, H. Ohki, K. Hotta, H. Ishida, M. Kiso, J. Carbohydr. Chem. 1991, 10, 493; A. Hasegawa, H. Ohki, T. Nagahama, H. Ishida, M. Kiso, Carbohydr. Res. 1991, 212, 277; T. J. Martin, R. R. Schmidt, Tetrahedron Lett. 1992, 33, 6123; A. V. Demchenko, G.-J. Boons, Tetrahedron Lett. 1998, 39, 3065; J. C. Castro-Palomino, Y. E. Tsvetkov, R. R. Schmidt, J. Am Chem. Soc. 1998, 120, 5434.
    • (1991) Carbohydr. Res. , vol.212 , pp. 277
    • Hasegawa, A.1    Ohki, H.2    Nagahama, T.3    Ishida, H.4    Kiso, M.5
  • 65
    • 0026658833 scopus 로고
    • Y. Ito, T. Ogawa, M. Numata, M. Sugimoto, J. Am. Chem. Soc. 1988; A. Hasegawa, T. Nagahama, H. Ohki, K. Hotta, H. Ishida, M. Kiso, J. Carbohydr. Chem. 1991, 10, 493; A. Hasegawa, H. Ohki, T. Nagahama, H. Ishida, M. Kiso, Carbohydr. Res. 1991, 212, 277; T. J. Martin, R. R. Schmidt, Tetrahedron Lett. 1992, 33, 6123; A. V. Demchenko, G.-J. Boons, Tetrahedron Lett. 1998, 39, 3065; J. C. Castro-Palomino, Y. E. Tsvetkov, R. R. Schmidt, J. Am Chem. Soc. 1998, 120, 5434.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6123
    • Martin, T.J.1    Schmidt, R.R.2
  • 66
    • 0032492977 scopus 로고    scopus 로고
    • Y. Ito, T. Ogawa, M. Numata, M. Sugimoto, J. Am. Chem. Soc. 1988; A. Hasegawa, T. Nagahama, H. Ohki, K. Hotta, H. Ishida, M. Kiso, J. Carbohydr. Chem. 1991, 10, 493; A. Hasegawa, H. Ohki, T. Nagahama, H. Ishida, M. Kiso, Carbohydr. Res. 1991, 212, 277; T. J. Martin, R. R. Schmidt, Tetrahedron Lett. 1992, 33, 6123; A. V. Demchenko, G.-J. Boons, Tetrahedron Lett. 1998, 39, 3065; J. C. Castro-Palomino, Y. E. Tsvetkov, R. R. Schmidt, J. Am Chem. Soc. 1998, 120, 5434.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3065
    • Demchenko, A.V.1    Boons, G.-J.2
  • 67
    • 0032503568 scopus 로고    scopus 로고
    • Y. Ito, T. Ogawa, M. Numata, M. Sugimoto, J. Am. Chem. Soc. 1988; A. Hasegawa, T. Nagahama, H. Ohki, K. Hotta, H. Ishida, M. Kiso, J. Carbohydr. Chem. 1991, 10, 493; A. Hasegawa, H. Ohki, T. Nagahama, H. Ishida, M. Kiso, Carbohydr. Res. 1991, 212, 277; T. J. Martin, R. R. Schmidt, Tetrahedron Lett. 1992, 33, 6123; A. V. Demchenko, G.-J. Boons, Tetrahedron Lett. 1998, 39, 3065; J. C. Castro-Palomino, Y. E. Tsvetkov, R. R. Schmidt, J. Am Chem. Soc. 1998, 120, 5434.
    • (1998) J. am Chem. Soc. , vol.120 , pp. 5434
    • Castro-Palomino, J.C.1    Tsvetkov, Y.E.2    Schmidt, R.R.3
  • 68
    • 0001776897 scopus 로고    scopus 로고
    • Eds.: D. G. Large, C. D. Warren, Marcel Dekker, New York
    • Y. Ichikawa, in Glycopeptides and Related Compounds (Eds.: D. G. Large, C. D. Warren), Marcel Dekker, New York, 1997, p. 79; C.-H. Wong, R, L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. 1995, 107, 453, 569; Angew. Chem. Int. Ed. Engl. 1995, 34, 412, 521.
    • (1997) Glycopeptides and Related Compounds , pp. 79
    • Ichikawa, Y.1
  • 69
    • 0000231155 scopus 로고
    • Y. Ichikawa, in Glycopeptides and Related Compounds (Eds.: D. G. Large, C. D. Warren), Marcel Dekker, New York, 1997, p. 79; C.-H. Wong, R, L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. 1995, 107, 453, 569; Angew. Chem. Int. Ed. Engl. 1995, 34, 412, 521.
    • (1995) Angew. Chem. , vol.107 , pp. 453
    • Wong, C.-H.1    Halcomb, R.L.2    Ichikawa, Y.3    Kajimoto, T.4
  • 70
    • 0029109703 scopus 로고
    • Y. Ichikawa, in Glycopeptides and Related Compounds (Eds.: D. G. Large, C. D. Warren), Marcel Dekker, New York, 1997, p. 79; C.-H. Wong, R, L. Halcomb, Y. Ichikawa, T. Kajimoto, Angew. Chem. 1995, 107, 453, 569; Angew. Chem. Int. Ed. Engl. 1995, 34, 412, 521.
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 412


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.