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Volumn 76, Issue 4, 2011, Pages 1045-1053

Stereoselective synthesis of 2-C-branched (acetylmethyl) oligosaccharides and glycoconjugates: Lewis acid-catalyzed glycosylation from 1,2-cyclopropaneacetylated sugars

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERICS; GLUCOSYL DONOR; GLYCOCONJUGATES; GLYCOSYL ACCEPTORS; GLYCOSYL DONORS; LEWIS ACID; LEWIS ACID CATALYSTS; STEREOSELECTIVE SYNTHESIS;

EID: 79951600548     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1016579     Document Type: Article
Times cited : (27)

References (54)
  • 22
    • 79951646416 scopus 로고    scopus 로고
    • Fraser-Reid B. Tatsuta K. Thiem J. Eds.; Springer-Verlag: Berlin, Germany
    • Du, Y. G.; Chen, Q.; Liu, J. In Glycoscience; Fraser-Reid, B.; Tatsuta, K.; Thiem, J., Eds.; Springer-Verlag: Berlin, Germany, 2008; pp 305-342.
    • (2008) Glycoscience , pp. 305-342
    • Du, Y.G.1    Chen, Q.2    Liu, J.3
  • 45
    • 0000455901 scopus 로고
    • Proton-proton coupling constants in a cyclopropane system: J = 0-6 Hz for a trans stereochemistry and J = 8-10 Hz for a cis stereochemistry. See:;
    • Proton-proton coupling constants in a cyclopropane system: J = 0-6 Hz for a trans stereochemistry and J = 8-10 Hz for a cis stereochemistry. See: Kawabata, N.; Nakagawa, T.; Nakao, T.; Yamashita, S. J. Org. Chem. 1977, 42, 3031-3035
    • (1977) J. Org. Chem. , vol.42 , pp. 3031-3035
    • Kawabata, N.1    Nakagawa, T.2    Nakao, T.3    Yamashita, S.4
  • 48
    • 0000669731 scopus 로고
    • Glycosyl triflates or the corresponding oxocarbenium triflates were used as glycosyl donors. See:;
    • Glycosyl triflates or the corresponding oxocarbenium triflates were used as glycosyl donors. See: Leroux, J.; Perlin, A. S. Carbohydr. Res. 1978, 67, 163-178
    • (1978) Carbohydr. Res. , vol.67 , pp. 163-178
    • Leroux, J.1    Perlin, A.S.2
  • 51
    • 79951624819 scopus 로고    scopus 로고
    • We hypothesized that trimethylsilyl enol ether 42 could form temporarily due to the fast coordination between the oxygen atom of acetyl and the trimethylsilyl cation, and decompose after nucleophilic attack because of the free proton. During this process, the trimethylsilyl enol ether 42 can hardly contribute to the stabilization of the oxocarbenium triflate.
    • We hypothesized that trimethylsilyl enol ether 42 could form temporarily due to the fast coordination between the oxygen atom of acetyl and the trimethylsilyl cation, and decompose after nucleophilic attack because of the free proton. During this process, the trimethylsilyl enol ether 42 can hardly contribute to the stabilization of the oxocarbenium triflate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.