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Volumn 128, Issue 35, 2006, Pages 11612-11619

Mechanistic studies and methods to prevent aglycon transfer of thioglycosides

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATES; CHEMICAL BONDS; COMPLEXATION; REACTION KINETICS;

EID: 33748365425     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja063247q     Document Type: Article
Times cited : (133)

References (66)
  • 2
    • 37849189010 scopus 로고    scopus 로고
    • Thioglycosides as glycosyl donors in oligosaccharide synthesis
    • Academic Press: New York
    • Garegg, P. J. Thioglycosides as glycosyl donors in oligosaccharide synthesis. In Advances In Carbohydrate Chemistry And Biochemistry; Academic Press: New York, 1997; Vol. 52, pp 179-205.
    • (1997) Advances in Carbohydrate Chemistry and Biochemistry , vol.52 , pp. 179-205
    • Garegg, P.J.1
  • 18
    • 13044269653 scopus 로고    scopus 로고
    • (b) Sofia, M. J. et al. J. Med. Chem. 1999, 42, 3193-3198.
    • (1999) J. Med. Chem. , vol.42 , pp. 3193-3198
    • Sofia, M.J.1
  • 24
    • 0002175452 scopus 로고    scopus 로고
    • Thiooligosaccharides in glycobiology
    • Springer Verlag: Berlin
    • For some recent reviews, see: (a) Driguez, H. Thiooligosaccharides in glycobiology. In Glycoscience Synthesis Of Substrate Analogs And Mimetics; Springer Verlag: Berlin, 1997; Vol. 187, pp 85-116.
    • (1997) Glycoscience Synthesis of Substrate Analogs and Mimetics , vol.187 , pp. 85-116
    • Driguez, H.1
  • 27
    • 0037012919 scopus 로고    scopus 로고
    • For some recent examples, see: (a) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995-2999.
    • (2002) J. Org. Chem. , vol.67 , pp. 2995-2999
    • Knapp, S.1    Myers, D.S.2
  • 46
    • 33748343197 scopus 로고    scopus 로고
    • note
    • For simplicity, the activated species has been represented as an oxocarbenium ion. However, other activated intermediates such as glycosyl triflates and dioxolenium ions may be present as well.
  • 47
    • 33748338806 scopus 로고    scopus 로고
    • note
    • While this paper focuses on other factors, it should be noted that the relative rates of decomposition of the activated intermediates and glycosylation may also affect the outcome of a reaction.
  • 54
    • 33748358372 scopus 로고    scopus 로고
    • note
    • In the absence of the glycosyl donor (imidate 4). the thioglycoside is stable to the reaction conditions.
  • 60
    • 33748350090 scopus 로고    scopus 로고
    • note
    • 2,6-Dimethylthiophenol was purchased from Oakwood Products. Inc. (West Columbia, SC) and is available from Aldrich (St. Louis, MO).
  • 61
    • 33748365673 scopus 로고    scopus 로고
    • note
    • The 2,6-dichlorophenyl aglycon was harder to install, harder to activate, and generally produced lower yields.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.