Fluorous oligosaccharide synthesis using a novel fluorous protective group

Organic Letters

Volumn 3, Issue 24, 2001, Pages 3947-3949

  Miura, Tsuyoshi ^a   Hirose, Yuriko ^a   Ohmae, Masashi ^a,b   Inazu, Toshiyuki ^a  

^a NOGUCHI INSTITUTE   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000574855     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016838o     Document Type: Article

References (25)

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2. Varki, A. Glycobiology 1993, 3, 97. Dwek, R. A. Chem. Rev. 1996, 96, 683. Blithe, D. L. Trends Glycosci. Glycotech. 1993, 5, 81.
3. Varki, A. Glycobiology 1993, 3, 97. Dwek, R. A. Chem. Rev. 1996, 96, 683. Blithe, D. L. Trends Glycosci. Glycotech. 1993, 5, 81.
4. Ando, H.; Manabe, S.; Nakahara, Y.; Ito, Y. J. Am. Chem. Soc. 2001, 123, 3848, and references therein.
5. Plante, O. J.; Palmacci, E. R.; Seeberger, P. H. Science 2001, 291, 1523.
6. Luo, Z.; Zhang, Q.; Oderatoshi, Y.; Curran, D. P. Science 2001, 291, 1766. Barrett, A. G. M.; Braddock, D. C.; Catterick, D.; Chadwick, D.; Henschke, J. P.; McKinnell, R. M. Synlett 2000, 847. Curran, D. P. Pure Appl. Chem. 2000, 72, 1649. Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174, and references therein.
7. Luo, Z.; Zhang, Q.; Oderatoshi, Y.; Curran, D. P. Science 2001, 291, 1766. Barrett, A. G. M.; Braddock, D. C.; Catterick, D.; Chadwick, D.; Henschke, J. P.; McKinnell, R. M. Synlett 2000, 847. Curran, D. P. Pure Appl. Chem. 2000, 72, 1649. Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174, and references therein.
8. Luo, Z.; Zhang, Q.; Oderatoshi, Y.; Curran, D. P. Science 2001, 291, 1766. Barrett, A. G. M.; Braddock, D. C.; Catterick, D.; Chadwick, D.; Henschke, J. P.; McKinnell, R. M. Synlett 2000, 847. Curran, D. P. Pure Appl. Chem. 2000, 72, 1649. Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174, and references therein.
9. Luo, Z.; Zhang, Q.; Oderatoshi, Y.; Curran, D. P. Science 2001, 291, 1766. Barrett, A. G. M.; Braddock, D. C.; Catterick, D.; Chadwick, D.; Henschke, J. P.; McKinnell, R. M. Synlett 2000, 847. Curran, D. P. Pure Appl. Chem. 2000, 72, 1649. Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1174, and references therein.
10. Wipf, P.; Reeves, J. T. Tetrahedron Lett. 1999, 40, 5139. Wipf, P.; Reeves, J. T. Tetrahedron Lett. 1999, 40, 4649. Röver, S.; Wipf, P. Tetrahedron Lett. 1999, 40, 5667. Wipf, P.; Reeves, J. T.; Balachandran, R.; Giuliano, K. A.; Hamel, E.; Day, B. W. J. Am. Chem. Soc. 2000, 122, 9391.
11. Wipf, P.; Reeves, J. T. Tetrahedron Lett. 1999, 40, 5139. Wipf, P.; Reeves, J. T. Tetrahedron Lett. 1999, 40, 4649. Röver, S.; Wipf, P. Tetrahedron Lett. 1999, 40, 5667. Wipf, P.; Reeves, J. T.; Balachandran, R.; Giuliano, K. A.; Hamel, E.; Day, B. W. J. Am. Chem. Soc. 2000, 122, 9391.
12. Wipf, P.; Reeves, J. T. Tetrahedron Lett. 1999, 40, 5139. Wipf, P.; Reeves, J. T. Tetrahedron Lett. 1999, 40, 4649. Röver, S.; Wipf, P. Tetrahedron Lett. 1999, 40, 5667. Wipf, P.; Reeves, J. T.; Balachandran, R.; Giuliano, K. A.; Hamel, E.; Day, B. W. J. Am. Chem. Soc. 2000, 122, 9391.
13. Wipf, P.; Reeves, J. T. Tetrahedron Lett. 1999, 40, 5139. Wipf, P.; Reeves, J. T. Tetrahedron Lett. 1999, 40, 4649. Röver, S.; Wipf, P. Tetrahedron Lett. 1999, 40, 5667. Wipf, P.; Reeves, J. T.; Balachandran, R.; Giuliano, K. A.; Hamel, E.; Day, B. W. J. Am. Chem. Soc. 2000, 122, 9391.
14. Curran, D. P.; Ferritto, R.; Hua, Y. Tetrahedron Lett. 1998, 39, 4937.
15. The tosylate 2 was prepared from perfluorooctylpropanol (DAIKIN, Tokyo) according to a literature procedure. Pozzi, G.; Cavazzini, M.; Quici, S.; Fontana, S. Tetrahedron Lett. 1997, 38, 7605.
16. Compound 4 was prepared from perfluorooctylpropanol by Jones oxidation.
17. +) 1046.1, found 1044.6.
18. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. Schmidt, R. R. Pure Appl. Chem. 1989, 61, 1257.
19. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. Schmidt, R. R. Pure Appl. Chem. 1989, 61, 1257.
20. 14) isomers.
21. +) 3578.4, found 3577.2.
22. Compounds 14, 15, 16, 17, and 19 were not detected by TLC from the toluene layer after three extractions with FC72. These results show that these compounds were quantitatively extracted with FC72.
23. +) 4046.5, found 4045.1.
24. Compounds 16 and 18 were obtained without complete optimization of glycosidation conditions.
25. Ryu, I.; Kreimermaan, S.; Niguma, T.; Minakata, S.; Komatsu, M.; Luo, Z.; Curran. D. P. Tretrahedron Lett. 2001, 42, 947.