Amberlyst 15 as a mild and effective activator for the glycosylation with disarmed glycosyl trichloroacetimidate donors

Tetrahedron

Volumn 63, Issue 10, 2007, Pages 2142-2147

  Tian, Qiang ^a   Zhang, Shuo ^a   Yu, Qian ^a   He, Mei Bo ^a   Yang, Jin Song ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Amberlyst 15; Glycosylation; Oligosaccharide; Trichloroacetimidate

Indexed keywords

ALCOHOL; AMINO ACID; GALACTOSE; LACTOSE; OLIGOSACCHARIDE; RESIN; RHAMNOSE; THIOL; TRICHLOROACETIMIDIC ACID;

ARTICLE; CHEMICAL STRUCTURE; GLYCOSYLATION; PRIORITY JOURNAL;

EID: 33846809079     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.12.091     Document Type: Article

References (32)

1. Sears P., and Wong C.H. Science 291 (2001) 2344
2. Seeberger P.H. Chem. Commun. (2003) 1115
3. Schmidt R.R. Angew. Chem., Int. Ed. Engl. 25 (1986) 212
4. Toshima K., and Tatsuta K. Chem. Rev. 93 (1993) 1530
5. Nicolaou K.C., and Mitchell H.J. Angew. Chem., Int. Ed. 40 (2001) 1576
6. Yu B., and Tao H. J. Org. Chem. 67 (2002) 9099
7. Schaubach R., Hemberger J., and Kinzy W. Liebigs Ann. Chem. (1991) 607
8. Zimmermann P., Bommer R., Bär T., and Schmidt R.R. J. Carbohydr. Chem. 7 (1988) 435
9. Haase W.C., and Seeberger P.H. Curr. Org. Chem. 4 (2000) 481
10. Adinolfi M., Barone G., Iadonisi A., and Schiattarella M. Synlett (2002) 269
11. Adinolfi M., Barone G., Iadonisi A., and Schiattarella M. Tetrahedron Lett. 43 (2002) 5573
12. Mukhopadhyay B., Maurer S.V., Rudolph N., Van Well R.M., Russell D.A., and Field R.A. J. Org. Chem. 70 (2005) 9059
13. Adinolfi M., Barone G., Iadonisi A., and Schiattarella M. Org. Lett. 5 (2003) 987
14. Adinolfi M., Iadonisi A., Ravidà A., and Schiattarella M. J. Org. Chem. 70 (2005) 5316
15. Schmidt R.R., and Jung K.-H. In: Hanessian S. (Ed). Preparative Carbohydrate Chemistry (1997), Dekker, New York, NY 283
16. Mukherjee D., Ray P.K., and Chowdhury U.S. Tetrahedron 57 (2001) 7701
17. Volker E., Reinhard B., and Margot W. Angew. Chem. 87 (1975) 747
18. Grayson E.J., Ward S.J., Hall A.L., Rendle P.M., Gamblin D.P., Batsanov A.S., and Davis B.G. J. Org. Chem. 70 (2005) 9740
19. Bebault G.M., and Dutton G.G.S. Can. J. Chem. 50 (1972) 3373
20. Backinowsky L.V., Tsvetkov Y.E., Balan N.F., Byramova N.E., and Kochetkov N.K. Carbohydr. Res. 85 (1980) 209
21. Kondo H., Aoki S., Ichikawa Y., Halcomb R.L., Ritzen H., and Wong C.H. J. Org. Chem. 59 (1994) 864
22. Filira F., Biondi L., Cavaggion F., Scolaro B., and Rocchi R. Int. J. Pept. Protein Res. 36 (1990) 86
23. Mahadevan A., Li C., and Fuchs P.L. Synth. Commun. 24 (1994) 3099
24. For the synthesis of thiooligosaccharide, see:
25. Pachamuthu K., and Schmidt R.R. Chem. Rev. 106 (2006) 160
26. Driguez H. Top. Curr. Chem. 187 (1997) 85 and references cited therein
27. Boons G.J. Tetrahedron 52 (1996) 1095
28. Demchenko A.V., and De Meo C. Tetrahedron Lett. 43 (2002) 8819
29. Yamada H., Harada T., and Takahashi T. J. Am. Chem. Soc. 116 (1994) 7919
30. Yu H., Yu B., Wu X.-Y., Hui Y.-Z., and Han X.-W. J. Chem. Soc., Perkin Trans. 1 (2000) 1445
31. Dasgupta S., Roy B., and Mukhopadhyay B. Carbohydr. Res. 341 (2006) 2708
32. For recent application of Amberlyst 15 as a mild acid activator of C2-amidoglycosylation with oxazoline donors, see:. Liu J., and Gin D.Y. J. Am. Chem. Soc. 124 (2002) 9789