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Volumn 5, Issue 11, 2003, Pages 1951-1954

Multivalent neoglycoconjugates by regiospecific cycloaddition of alkynes and azides using organic-soluble copper catalysts

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZIDE; COPPER COMPLEX;

EID: 0141629513     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034534r     Document Type: Article
Times cited : (332)

References (39)
  • 7
    • 0002773690 scopus 로고
    • Lee, Y. C., Lee, R. T., Eds.; Academic Press: San Diego
    • (a) Lee, R. T.; Lee, Y. C. In Neoglycoconjugates; Lee, Y. C., Lee, R. T., Eds.; Academic Press: San Diego, 1994, p 23.
    • (1994) Neoglycoconjugates , pp. 23
    • Lee, R.T.1    Lee, Y.C.2
  • 16
    • 0141825082 scopus 로고    scopus 로고
    • note
    • Presence of an aromatic heterocyclic group next to the glycosidic bond has been pointed out as contributing positively to the interaction of neoglyconjugates with lectins by increasing the hydrophobicity. See ref 5d.
  • 27
    • 0037021535 scopus 로고    scopus 로고
    • For applications of this methodology, see: (c) Fazio, F.; Bryan, M. C.; Blixt, O.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 2002, 124, 14397. (d) Wang, Q.; Chan, R. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 14397
    • Fazio, F.1    Bryan, M.C.2    Blixt, O.3    Paulson, J.C.4    Wong, C.-H.5
  • 36
    • 0037073885 scopus 로고    scopus 로고
    • Application of microwave irradiation in the 1,3-dipolar cycloaddition of alkynes and azides has been only very limited up to the present: (e) Louërat, F.; Bougrin, K.; Loupy, A.; Ochoa de Retana, A. M.; Pagalday, J.; Palacios, F. Heterocycles 1998, 48, 161.
    • (2002) J. Org. Chem. , vol.67 , pp. 9077
    • Katritzky, A.R.1    Singh, A.K.2
  • 37
    • 0141601981 scopus 로고    scopus 로고
    • note
    • NOE difference spectroscopy has been used for the unambiguous assignment as the 1,4-regioisomer in selected cases.
  • 38
    • 0001194625 scopus 로고
    • Substitution of the natural O-glycosides by S- or C-glycosides is a normal alternative in the synthesis of carbohydrate mimics in order to enhance the stability of the glycosidic linkage towards enzymatic hydrolysis: Bertozzi, C. R.; Bednarski, M. D. J. Am. Chem. Soc. 1992, 114, 5543.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5543
    • Bertozzi, C.R.1    Bednarski, M.D.2
  • 39
    • 0141490446 scopus 로고    scopus 로고
    • note
    • 3P·CuI] (10-20 mmol %) in toluene (25 mL) was irradiated at 850 W (100% power) in a microwave oven (LG MG-5507D) for periods of 2 min, allowing the solution to cool heating intervals, until TLC or the IR spectra of the reaction mixture showed complete disappearance of the starting material. The reaction mixture was evaporated and the crude purified in a short flash column chromatography to yield the 1,2,3-triazole derivative.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.