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Volumn 44, Issue 50, 2003, Pages 9039-9041

Stereoselective approach to C-glycosylasparagines

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; AMIDE; ASPARAGINE DERIVATIVE; CARBENE; CARBOHYDRATE DERIVATIVE; CARBON; GLYCINE IMINE; GLYCOPEPTIDE; IMINE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0242626820     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.212     Document Type: Article
Times cited : (22)

References (26)
  • 10
    • 0036462601 scopus 로고    scopus 로고
    • Roth J. Chem. Rev. 102:2002;285-303.
    • (2002) Chem. Rev. , vol.102 , pp. 285-303
    • Roth, J.1
  • 12
    • 85030952176 scopus 로고    scopus 로고
    • See for example: (a) Damkaci, F.; DeShong, P. J. Am. Chem. Soc. 2003, 125, 4408-4409; (b) Zhang, H.; Wang, Y.; Thurmer, R.; Al-Qawasmeh, R. A.; Voelter, W. Pol. J. Chem. 1999, 73, 101-115; (c) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis 1999, 162-165; (d) Takeda, T.; Kojima, K.; Ogihara, Y. Carbohydr. Res. 1993, 243, 79-89; (e) Teshima, T.; Nakajima, K.; Takahashi, M.; Shiba, T. Tetrahedron Lett. 1992 33, 363-366.
    • See for example: (a) Damkaci, F.; DeShong, P. J. Am. Chem. Soc. 2003, 125, 4408-4409; (b) Zhang, H.; Wang, Y.; Thurmer, R.; Al-Qawasmeh, R. A.; Voelter, W. Pol. J. Chem. 1999, 73, 101-115; (c) Mizuno, M.; Muramoto, I.; Kobayashi, K.; Yaginuma, H.; Inazu, T. Synthesis 1999, 162-165; (d) Takeda, T.; Kojima, K.; Ogihara, Y. Carbohydr. Res. 1993, 243, 79-89; (e) Teshima, T.; Nakajima, K.; Takahashi, M.; Shiba, T. Tetrahedron Lett. 1992 33, 363-366.
  • 14
    • 85030952281 scopus 로고    scopus 로고
    • For examples of bioactive peptides incorporating ketomethylene isosteres, see: (a) Steinmetzer, T.; Zhu, B. Y.; Konishi, Y. J. Med. Chem. 1999, 42, 3109-3115; (b) Dragovich, P. S.; Prins, T. J.; Zhou, R.; Fuhrman, S. A.; Patick, A. K.; Matthews, D. A.; Ford, C. E.; Meador, J. W.; Ferre, R. A.; Worland, S. T. J. Med. Chem. 1999, 42, 1203-1212 and references cited therein.
    • For examples of bioactive peptides incorporating ketomethylene isosteres, see: (a) Steinmetzer, T.; Zhu, B. Y.; Konishi, Y. J. Med. Chem. 1999, 42, 3109-3115; (b) Dragovich, P. S.; Prins, T. J.; Zhou, R.; Fuhrman, S. A.; Patick, A. K.; Matthews, D. A.; Ford, C. E.; Meador, J. W.; Ferre, R. A.; Worland, S. T. J. Med. Chem. 1999, 42, 1203-1212 and references cited therein.
  • 15
    • 0035799866 scopus 로고    scopus 로고
    • For examples of synthetic approaches to N-glycosylasparagines that do allow direct access to ketomethylene isosteres, see: (a) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375-1378; (b) Werner, R. M.; Williams, L. M.; Davis, J. T.; Tetrahedron Lett. 1998, 39, 9135-9138.
    • For examples of synthetic approaches to N-glycosylasparagines that do allow direct access to ketomethylene isosteres, see: (a) Westermann, B.; Walter, A.; Flörke, U.; Altenbach, H.-J. Org. Lett. 2001, 3, 1375-1378; (b) Werner, R. M.; Williams, L. M.; Davis, J. T.; Tetrahedron Lett. 1998, 39, 9135-9138.
  • 17
    • 85030941231 scopus 로고    scopus 로고
    • Control experiments employing both achiral and (R)-selective PTC's established that the asymmetric alkylations outlined here proceed with ≥90% d.e.
    • Control experiments employing both achiral and (R)-selective PTC's established that the asymmetric alkylations outlined here proceed with ≥90% d.e.
  • 26
    • 84903914524 scopus 로고    scopus 로고
    • Lygo, B. Phase-Transfer Reactions, In Rodd's Chemistry of Carbon Compounds, Vol. V; Asymmetric Catalysis; Elsevier Science Ltd.: Oxford, 2001; pp. 101-150.
    • Lygo, B. Phase-Transfer Reactions, In Rodd's Chemistry of Carbon Compounds, Vol. V; Asymmetric Catalysis; Elsevier Science Ltd.: Oxford, 2001; pp. 101-150.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.