Synthesis of - C -glycosides by samarium diiodide mediated coupling of glycosyl pyridyl sulfones with alkenes

Synlett

Volumn , Issue 16, 2011, Pages 2410-2414

  Li, Gen ^a   Xiong, De Cai ^a   Ye, Xin Shan ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

C glycosides; coupling reaction; glycosyl 2 pyridyl sulfones; samarium diiodide

Indexed keywords

ACRYLIC ACID METHYL ESTER; ALKENE DERIVATIVE; GLYCOSIDE; GLYCOSYL 2 PYRIDYL SULFONE DERIVATIVE; GLYCOSYL PYRIDYL SULFONE DERIVATIVE; PROPIONIC ACID; SAMARIUM DIIODIDE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ELIMINATION REACTION; HYDROBORATION; OXIDATION; OXIDATIVE COUPLING; PROCESS OPTIMIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 80053053646     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1261230     Document Type: Article

References (63)

1. Compain P, Martin O R., Bioorg. Med. Chem. 2001 9 3077
2. Bililign T, Griffith B R., Thorson J S., Nat. Prod. Rep. 2005 22 742
3. Nicolaou K C., Mitchell [nl]H J., Angew. Chem. Int. Ed. 2001 40 1576
4. Levy D E., Tang C, The Chemistry of C-Glycosides Pergamon Tarrytown (NY) 1995
5. Du Y, Linhardt R J., Vlahov I R., Tetrahedron 1998 54 9913
6. Dondoni A, Marra A, Chem. Rev. 2000 100 4395
7. Somsk L, Chem. Rev. 2001 101 81
8. Koester D C., Holkenbrink A, Werz D B., Synthesis 2010 3217
9. McGarvey G J., LeClair C A., Schmidtmann B A., Org. Lett. 2008 10 4727
10. Crich D, Sharma I, Org. Lett. 2008 10 4731
11. Gong H, Gagné M R., J. Am. Chem. Soc. 2008 130 12177
12. Gong H, Sinisi R, Gagné M R., J. Am. Chem. Soc. 2007 129 1908
13. Adlington R M., Baldwin J E., Basak A, Kozyrod R P., J. Chem. Soc., Chem. Commun. 1983 944
14. Dupuis J, Giese B, Hartung J, Leising M, Korth H.-G, Sustmann R, J. Am. Chem. Soc. 1985 107 4332
15. Praly J.-P, Ardakani A S., Bruyre I, Marie-Luce C, Qin [nl]B B., Carbohydr. Res. 2002 337 1623
16. DeShong P, Slough G A., Elango V, Carbohydr. Res. 1987 171 342
17. Parrish J D., Little R D., Org. Lett. 2002 4 1439
18. Readman S K., Marsden S P., Hodgson A, Synlett 2000 1628
19. Micskei K, Juhsz Z, Ratkovi Z R., Somsk L, Tetrahedron Lett. 2006 47 6117
20. Gong H, Andrews R S., Zuccarello J L., Lee S J., Gagné M R., Org. Lett. 2009 11 879
21. Andrews R S., Becker J J., Gagné M R., Angew. Chem. Int. Ed. 2010 49 7274
22. 2 chemistry, see:, Kagan H B., Tetrahedron 2003 59 10351
23. Steel P G., J. Chem. Soc., Perkin Trans. 1 2001 2727
24. Molander G A., Chem. Rev. 1992 92 29
25. Hung S.-C, Wong C.-H, Angew. Chem., Int. Ed. Engl. 1996 35 2671
26. Jarreton O, Skrydstrup T, Beau J.-M, Tetrahedron Lett. 1997 38 1767
27. Skrydstrup T, Jarreton O, Mazéas D, Urban D, Beau J.-M, Chem. Eur. J. 1998 4 655
28. Miquel N, Doisneau G, Beau J.-M, Chem. Commun. 2000 2347
29. Miquel N, Doisneau G, Beau J.-M, Angew. Chem. Int. Ed. 2000 39 4111
30. Chiara J L., Sesmilo E, Angew. Chem. Int. Ed. 2002 41 3242
31. Mikkelsen L M., Skrydstrup T, J. Org. Chem. 2003 68 2123
32. Andersen L, Mikkelsen L M., Beau [nl]J.-M, Skrydstrup T, Synlett 1998 1393
33. Urban D, Skrydstrup T, Beau J.-M, Chem. Commun. 1998 955
34. Ren Z.-X, Yang Q, Price K N., Chen T, Nygren C, Turner J F. C., Baker D C., Carbohydr. Res. 2007 342 1668
35. Vlahov I R., Vlahova P I., Linhardt R J., J. Am. Chem. Soc. 1997 119 1480
36. Polat T, Du Y, Linhardt R J., Synlett 1998 1195
37. Du Y, Linhardt R J., Carbohydr. Res. 1998 308 161
38. Bazin H G., Du Y, Polat T, Linhardt R J., J. Org. Chem. 1999 64 7254
39. Wang Q, Linhardt R J., J. Org. Chem. 2003 68 2668
40. Abdallah Z, Doisneau G, Beau J.-M, Angew. Chem. Int. Ed. 2003 42 5209
41. Malapelle A, Abdallah Z, Doisneau G, Beau J.-M, Angew. Chem. Int. Ed. 2006 45 6016
42. Malapelle A, Coslovi A, Doisneau G, Beau J.-M, Eur. J. Org. Chem. 2007 3145
43. Papin C, Doisneau G, Beau J.-M, Chem. Eur. J. 2009 15 53
44. Chénedé A, Perrin E, Reka E D., Sina P, Synlett 1994 420
45. Mazéas D, Skrydstrup T, Doumeix O, Beau J.-M, Angew. Chem., Int. Ed. Engl. 1994 33 1383
46. Skrydstrup T, Mazéas D, Elmouchir M, Doisneau G, Riche C, Chiaroni A, Beau J.-M, Chem. Eur. J. 1997 3 1342
47. Doisneau G, Beau J.-M, Tetrahedron Lett. 1998 39 3477
48. Inanaga J, Handa Y, Tabuchi T, Otsubo K, Yamaguchi M, Hanamoto T, Tetrahedron Lett. 1991 32 6557
49. Cabrera A, Alper H, Tetrahedron Lett. 1992 33 5007
50. Inanaga J, Ishikawa M, Yamaguchi M, Chem. Lett. 1987 1485
51. Krief A, Laval A M., Chem. Rev. 1999 99 745
52. Machrouhi F, Hamman B, Namy J.-L, Kagan H B., Synlett 1996 633
53. Keck G E., Wager C A., Sell T, Wager T T., J. Org. Chem. 1999 64 2172
54. Tarnopolsky A, Hoz S, J. Am. Chem. Soc. 2007 129 3402
55. Cook B N., Bhakta S, Biegel T, Bowman K G., Armstrong J I., Hemmerich S, Bertozzi C R., J. Am. Chem. Soc. 2000 122 8612
56. Miller G J., Gardiner [nl]J M., Org. Lett. 2010 12 5262
57. Juhsz Z, Micskei K, Gl E, Somsk L, Tetrahedron Lett. 2007 48 7351
58. Cui J, Horton D, Carbohydr. Res. 1998 309 319
59. SanMartin R, Tavassoli B, Walsh K E., Walter D S., Gallagher T, Org. Lett. 2000 2 4051
60. Grant L, Liu Y, Walsh K E., Walter D S., Gallagher T, Org. Lett. 2002 4 4623
61. Liu Y, Gallagher T, Org. Lett. 2004 6 2445
62. Gotanda K, Matsugi M, Suemure M, Sano A, Oka M, Kita Y, Tetrahedron 1999 55 10315
63. Procter D J., Flowers R A. II, Skrydstrup T, Organic Synthesis Using Samarium Diiodide RSC Cambridge 2009 188-189