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Volumn 45, Issue 27, 2004, Pages 5197-5201

Synthesis of C-aryl-Δ2,3-glycopyranosides via uncatalyzed addition of triarylindium reagents to glycals

Author keywords

C glycosidation; Glycals; Triorganoindiums

Indexed keywords

ACETIC ACID; ALKYNE DERIVATIVE; CARBENOID; GLUCONATE CALCIUM; GLYCOPYRANOSIDE; GLYCOSIDE; INDIUM; ION; LEWIS ACID; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; REAGENT; VINYL DERIVATIVE;

EID: 2942545089     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.046     Document Type: Article
Times cited : (31)

References (54)
  • 19
    • 2942531139 scopus 로고    scopus 로고
    • note
    • 2 were completely homogenous, reactions performed in ether or toluene had visible white precipitates that did not dissolve throughout the course of the reaction
  • 20
    • 2942532976 scopus 로고    scopus 로고
    • ′(Table2)
    • ′ (Table 2)
  • 24
    • 2942596521 scopus 로고    scopus 로고
    • note
    • -) prevents the addition of nucleophiles to the less-hindered β-face of the oxonium ion. See Ref. [12a] for a discussion of solvent effects on the stereochemistry of glycosidation
  • 26
    • 33751386591 scopus 로고
    • ′ of α-glycopyranoside anomers will be shielded with respect to the corresponding carbons of the β-anomers:
    • ′ of α-glycopyranoside anomers will be shielded with respect to the corresponding carbons of the β-anomers: Brakta M., Farr R.N., Chaguir B., Massiot G., Lavaud C., Anderson W.R., Sinou D., Daves G.D. J. Org. Chem. 58:1993;2992-2998
    • (1993) J. Org. Chem. , vol.58 , pp. 2992-2998
    • Brakta, M.1    Farr, R.N.2    Chaguir, B.3    Massiot, G.4    Lavaud, C.5    Anderson, W.R.6    Sinou, D.7    Daves, G.D.8
  • 32
    • 2942561041 scopus 로고    scopus 로고
    • note
    • The weakness of the indium-carbon bond (∼40 kcal/mol) has been cited as a possible reason for the atom efficiency of indium reagents in transferring their organic ligands (replacing them preferentially with more electronegative substitutents, such as halides); see Refs. 9 and 6
  • 36
    • 0003625413 scopus 로고
    • For previous literature on C-aryl glycoside synthesis, see:
    • For previous literature on C-aryl glycoside synthesis, see: Jaramillo C., Knapp S. Synthesis. 1993;1-20
    • (1993) Synthesis , pp. 1-20
    • Jaramillo, C.1    Knapp, S.2
  • 49
    • 0004282354 scopus 로고
    • There appears to be dispute over the structures of Epiorientin and Parkinsonin B; see
    • There appears to be dispute over the structures of Epiorientin and Parkinsonin B; see Besson E., Chopin J., Gunasegaran R., Nair A.G.R. Phytochemistry. 19:1980;2787-2788
    • (1980) Phytochemistry , vol.19 , pp. 2787-2788
    • Besson, E.1    Chopin, J.2    Gunasegaran, R.3    Nair, A.G.R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.