Fullerene glycoconjugates: A general synthetic approach via cycloaddition of per-O-acetyl glycosyl azides to [60]fullerene

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 9031-9034

  Yashiro, Arihiro ^a   Nishida, Yoshihiro ^a   Ohno, Masatomi ^a   Eguchi, Shoji ^a   Kobayashi, Kazukiyo ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Azides; Cycloadditions; Fullerenes; Glycosides; Singlet oxygen

Indexed keywords

FULLERENE; GLYCOSIDE; OLIGOSACCHARIDE;

ACETYLATION; ARTICLE; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032481023     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02047-4     Document Type: Article

References (14)

1. [1] Varki A. Glycobiology 1993 ; 3 : 97-130.
2. [2] Varki A. Proc. Natl. Acad. Sci. U.S.A. 1994 ; 91 : 7390-7397.
3. [3] Sharon N, Lis H. Sci Am. 1993 ; 1 : 74-81.
4. [4] Kobayashi K, Kobayashi A, Tobe S, Akaike T. in Neoglycoconjugates: Preparation and Applications (Lee YC, Lee RT, eds.) Academic Press, San Diego 1994 ; 261-282.
5. [5] Kobayashi K, Tsuchida A, Usui A, Akaike T. Macromolecules 1997 ; 30 : 2016-2020
6. [6] For a review of biological application of fullerene, Jensen AW, Wilson SR, Schuster DI. Bioorg. Med. Chem. 1994 ; 4 : 767-779.
7. [7] Vasella A, Uhlmann P, Waldraff CAA, Diederich F, Thilgen C. Angew. Chem. Int Ed. Engl. 1992 ; 31 : 1388-1390.
8. [8] Banks MR, Cadogan JIG, Gosney I, Hodgson PKG, Langridge-Smith PRR, Millar JRA, Taylor A. J. Chem. Soc., Chem. Commun. 1995 : 885-886.
9. [9] Cardullo F, Diederich F, Echegoyen L, Habicher T, Jayaraman N, Leblanc RM, Stoddart JF, Wang S. Langmuir 1998 ; 14 : 1955-1959.
10. [10] Prato M, Li QC, Wudl F. J. Am. Chem. Soc. 1993 ; 115 : 1148-1150.
11. 13C signal at ca. 160 ppm as well as by FAB-MS measurement.
12. [12] Grosser T, Prato M, Lucchini V, Hirsch A, Wudl F. Angew. Chem. Int. Ed. Engl. 1995 ; 34 : 1343-1345.
13. [13] Hummelen JC, Prato M, Wudl F. J. Am. Chem. Soc. 1995 ; 117 ; 7003-7004.
14. [14] Schick G, Grosser T, Hirsch A. J. Chem. Soc., Chem. Commun. 1995 : 2289-2290.