A facile and convenient synthesis of disarmed glycosyl fluorides using in situ-generated iodine monofluoride (see Ref. 1)

Tetrahedron Letters

Volumn 53, Issue 42, 2012, Pages 5631-5634

  Mugunthan, G ^a   Kartha, K P Ravindranathan ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Applications of interhalogens; Glycosyl fluorides; Iodine monofluoride; Silver fluoride iodine; Thioglycosides

Indexed keywords

FLUORIDE; GLYCOSIDE; IODINE DERIVATIVE; PYRANOSIDE;

ARTICLE; CONTROLLED STUDY; FEASIBILITY STUDY; GLYCOSYLATION; INTERMETHOD COMPARISON; ROOM TEMPERATURE; SYNTHESIS;

EID: 84866239052     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.08.024     Document Type: Article

References (40)

1. Iodine and its interhalogen compounds: Versatile reagents in carbohydrate chemistry XXV. For Part XXIV see K.V. Rao, P.R. Patil, S. Atmakuri, and K.P.R. Kartha Carbohydr. Res. 345 2010 2709 2713
2. D.H. Brauns J. Am. Chem. Soc. 45 1923 833 835
3. T. Mukaiyama, Y. Murai, and S. Shoda Chem. Lett. 10 1981 431 432
4. K. Toshima Carbohydr. Res. 327 2000 15 26
5. T. Mukaiyama, Y. Hashimoto, and S. Shoda Chem. Lett. 12 1983 935 938
6. Y. Araki, K. Watanabe, F.-H. Kuan, K. Itoh, N. Kobayashi, and Y. Ishido Carbohydr. Res. 127 1984 C-5 C-9
7. M. Hayashi, S. Hashimoto, and R. Noyori Chem. Lett. 13 1984 1747 1750
8. W.A. Szarek, and G. Grynkiewicz Chem. Lett. 13 1984 1751 1754
9. W. Rosenbrook Jr., D.A. Riley, and P.A. Lartey Tetrahedron Lett. 26 1985 3 4
10. G.H. Posner, and S.R. Haines Tetrahedron Lett. 26 1985 5 8
11. H. Kunz, and W. Sanger Helv. Chim. Acta 68 1985 283 287
12. B. Ernst, and T. Winkler Tetrahedron Lett. 30 1989 3081 3084
13. R. Miethchen, C. Hager, and M. Hein Synthesis 1997 159 161
14. M.D. Burkart, Z. Zhang, S.-C. Hung, and C.-H. Wong J. Am. Chem. Soc. 119 1997 11743 11746
15. A. L'Heureux, F. Beaulieu, C. Bennett, D.R. Bill, S. Clayton, F. LaFlamme, M. Mirmehrabi, S. Tadayon, D. Tovell, and M. Couturier J. Org. Chem. 75 2010 3401 3411
16. S. Kobayashi, A. Yoneda, T. Fukuhara, and S. Hara Tetrahedron Lett. 45 2004 1287 1289
17. J. Yin, D.S. Zarkowsky, D.W. Thomas, M.M. Zhao, and M.A. Huffman Org. Lett. 6 2004 1465 1468
18. T. Umemoto, R.P. Singh, Y. Xu, and N. Saito J. Am. Chem. Soc. 132 2010 18199 18205
19. J.C. Lpez, J. Ventura, C. Uriel, A.M. Gmez, and B. Fraser-Reid Org. Lett. 11 2009 4128 4131
20. T. Gabriel, G. Kolp, D. Peters, and R. Miethchen J. Fluorine Chem. 54 1991 383
21. R. Miethchen, and T. Gabriel J. Fluorine Chem. 67 1994 11 15
22. W. Bröder, and H. Kunz Carbohydr. Res. 249 1993 221 241
23. M. Palme, and A. Vasella Helv. Chim. Acta 78 1995 959 969
24. B. Helferich, and R. Gootz Ber. 61 1929 2505 2507
25. F. Micheel, A. Klerner, and R. Flitsch Chem. Ber. 91 1958 663 667
26. K. Igarashi, T. Honma, and J. Irisawa Carbohydr. Res. 13 1970 49 55
27. R. Miethcen, and G. Kolp J. Fluorine Chem. 60 1993 49 55
28. K.D. Goggin, J.F. Lambert, and S.W. Walinsky Synlett 1994 162 164
29. K.C. Nicolaou, R.E. Dolle, D.P. Papahatjis, and J.L. Randall J. Am. Chem. Soc. 106 1984 4189 4192
30. S. Caddick, L. Gazzard, W.B. Motherwell, and J.A. Wilkinson Tetrahedron 52 1996 149 156
31. K.-T. Huang, and N. Winssinger Eur. J. Org. Chem. 2007 1887 1890
32. J.L. Lpez, P. Bernal-Albert, C. Uriel, S. Valverde, and A.M. Gmez J. Org. Chem. 72 2007 10268 10271
33. Reviewed in K. P. R Kartha and Robert Field, Best synthetic methods: Carbohydrates 2003, 121-145.
34. K.P.R. Kartha, T.S. Kärkkäinen, S.J. Marsh, and R.A. Field Synlett 2001 260 262
35. K.P.R. Kartha, and R.A. Field Tetrahedron Lett. 47 1997 8233 8236
36. L.D. Hall, and J.F. Manville Can. J. Chem. 47 1969 361 377
37. Y.V. Voznij, L.N. Koikov, and A.A. Galoyan Carbohydr. Res. 132 1984 339 341
38. D.H. Brauns Bur. Standards J. Res. 7 1931 573 583
39. K. Nishiyama, S. Esaki, I. Deguchi, N. Sugiyama, and S. Kamiya Biosci. Biotechnol. Biochem. 57 1993 107 114
40. P.W. Kent, and S.D. Dimitrijevich J. Fluorine Chem. 10 1977 455 478