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Volumn 338, Issue 15, 2003, Pages 1531-1534

Environmentally benign and stereoselective formation of β-mannosidic linkages utilizing 2,3-di-O-benzyl-4,6-O-benzylidene-protected mannopyranosyl phosphite and montmorillonite K-10

Author keywords

Glycosidation; Glycosyl phosphite; Montmorillonite K 10; Solid acid; Mannopyranoside

Indexed keywords

AROMATIC COMPOUNDS; ENVIRONMENTAL ENGINEERING; STEREOCHEMISTRY;

EID: 0037629426     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(03)00234-9     Document Type: Article
Times cited : (19)

References (44)
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    • Watanabe, Y.1    Nakamoto, C.2    Yamamoto, T.3    Ozaki, S.4
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    • For the pioneering works on phoshite glycosidation, see: (a) Martin, T. J.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 6123-6126; (b) Kondo, H.; Ichikawa, Y.; Wong, C. -H. J. Am. Chem. Soc. 1992, 114, 8748-8750; (c) Sim, M. M.; Kondo, H.; Wong, C. -H. J. Am. Chem. Soc. 1993, 115, 2260-2267; (d) Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C. -H. J. Org. Chem. 1994, 59, 864-877; (e) Watanabe, Y.; Nakamoto, C.; Ozaki, S. Synlett 1993, 115-116; (f) Watanabe, Y.; Nakamoto, C.; Yamamoto, T.; Ozaki, S. Tetrahedron 1994, 50, 6523-6536; (g) Hashimoto, S.; Umeo, K.; Sano, A.; Watanabe, N.; Nakajima, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 2251-2254; (h) Hashimoto, S.; Sano, A.; Sakamoto, H.; Nakajima, M.; Yamagiya, Y.; Ikegami, S. Synlett 1995, 1271-1273; (i) Tanaka, H.; Sakamoto, H.; Nakamura, S.; Nakajima, M.; Hashimoto, S. Chem. Commun. 1999, 1259-1260; (j) Sakamoto, H.; Nakamura, S.; Tsuda, T.; Hashimoto, S. Tetrahedron Lett. 2000, 41, 7691-7695.
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    • For the pioneering works on phoshite glycosidation, see: (a) Martin, T. J.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 6123-6126; (b) Kondo, H.; Ichikawa, Y.; Wong, C. -H. J. Am. Chem. Soc. 1992, 114, 8748-8750; (c) Sim, M. M.; Kondo, H.; Wong, C. -H. J. Am. Chem. Soc. 1993, 115, 2260-2267; (d) Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C. -H. J. Org. Chem. 1994, 59, 864-877; (e) Watanabe, Y.; Nakamoto, C.; Ozaki, S. Synlett 1993, 115-116; (f) Watanabe, Y.; Nakamoto, C.; Yamamoto, T.; Ozaki, S. Tetrahedron 1994, 50, 6523-6536; (g) Hashimoto, S.; Umeo, K.; Sano, A.; Watanabe, N.; Nakajima, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 2251-2254; (h) Hashimoto, S.; Sano, A.; Sakamoto, H.; Nakajima, M.; Yamagiya, Y.; Ikegami, S. Synlett 1995, 1271-1273; (i) Tanaka, H.; Sakamoto, H.; Nakamura, S.; Nakajima, M.; Hashimoto, S. Chem. Commun. 1999, 1259-1260; (j) Sakamoto, H.; Nakamura, S.; Tsuda, T.; Hashimoto, S. Tetrahedron Lett. 2000, 41, 7691-7695.
    • (1995) Synlett , pp. 1271-1273
    • Hashimoto, S.1    Sano, A.2    Sakamoto, H.3    Nakajima, M.4    Yamagiya, Y.5    Ikegami, S.6
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    • 0033532915 scopus 로고    scopus 로고
    • For the pioneering works on phoshite glycosidation, see: (a) Martin, T. J.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 6123-6126; (b) Kondo, H.; Ichikawa, Y.; Wong, C. -H. J. Am. Chem. Soc. 1992, 114, 8748-8750; (c) Sim, M. M.; Kondo, H.; Wong, C. -H. J. Am. Chem. Soc. 1993, 115, 2260-2267; (d) Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C. -H. J. Org. Chem. 1994, 59, 864-877; (e) Watanabe, Y.; Nakamoto, C.; Ozaki, S. Synlett 1993, 115-116; (f) Watanabe, Y.; Nakamoto, C.; Yamamoto, T.; Ozaki, S. Tetrahedron 1994, 50, 6523-6536; (g) Hashimoto, S.; Umeo, K.; Sano, A.; Watanabe, N.; Nakajima, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 2251-2254; (h) Hashimoto, S.; Sano, A.; Sakamoto, H.; Nakajima, M.; Yamagiya, Y.; Ikegami, S. Synlett 1995, 1271-1273; (i) Tanaka, H.; Sakamoto, H.; Nakamura, S.; Nakajima, M.; Hashimoto, S. Chem. Commun. 1999, 1259-1260; (j) Sakamoto, H.; Nakamura, S.; Tsuda, T.; Hashimoto, S. Tetrahedron Lett. 2000, 41, 7691-7695.
    • (1999) Chem. Commun. , pp. 1259-1260
    • Tanaka, H.1    Sakamoto, H.2    Nakamura, S.3    Nakajima, M.4    Hashimoto, S.5
  • 38
    • 0034734698 scopus 로고    scopus 로고
    • For the pioneering works on phoshite glycosidation, see: (a) Martin, T. J.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 6123-6126; (b) Kondo, H.; Ichikawa, Y.; Wong, C. -H. J. Am. Chem. Soc. 1992, 114, 8748-8750; (c) Sim, M. M.; Kondo, H.; Wong, C. -H. J. Am. Chem. Soc. 1993, 115, 2260-2267; (d) Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C. -H. J. Org. Chem. 1994, 59, 864-877; (e) Watanabe, Y.; Nakamoto, C.; Ozaki, S. Synlett 1993, 115-116; (f) Watanabe, Y.; Nakamoto, C.; Yamamoto, T.; Ozaki, S. Tetrahedron 1994, 50, 6523-6536; (g) Hashimoto, S.; Umeo, K.; Sano, A.; Watanabe, N.; Nakajima, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 2251-2254; (h) Hashimoto, S.; Sano, A.; Sakamoto, H.; Nakajima, M.; Yamagiya, Y.; Ikegami, S. Synlett 1995, 1271-1273; (i) Tanaka, H.; Sakamoto, H.; Nakamura, S.; Nakajima, M.; Hashimoto, S. Chem. Commun. 1999, 1259-1260; (j) Sakamoto, H.; Nakamura, S.; Tsuda, T.; Hashimoto, S. Tetrahedron Lett. 2000, 41, 7691-7695.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 7691-7695
    • Sakamoto, H.1    Nakamura, S.2    Tsuda, T.3    Hashimoto, S.4
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    • Montmorillonite K-10 was purchased from Aldrich Chemical Company, Inc. and dried at 200°C/1 mm Hg for 12 h before use
    • Montmorillonite K-10 was purchased from Aldrich Chemical Company, Inc. and dried at 200°C/1 mm Hg for 12 h before use.


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