Ferric sulfate hydrate-catalyzed O-glycosylation using glycals with or without microwave irradiation

Tetrahedron

Volumn 64, Issue 2, 2008, Pages 339-344

  Zhang, Guisheng ^a   Liu, Qingfeng ^a   Shi, Lei ^a   Wang, Jiuxia ^a  

^a HENAN NORMAL UNIVERSITY   (China)

Author keywords

2,3 Unsaturated O glycosides; Ferric sulfate hydrate; Ferrier rearrangement; O Glycosylation; Peracetyl or perbenzyl glucal

Indexed keywords

FERRIC SULFATE; GLYCOSIDE; O GLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; GLYCOSYLATION; MICROWAVE IRRADIATION; PRIORITY JOURNAL;

EID: 36448933120     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.097     Document Type: Article

References (59)

1. Schreiber S.L. Science 287 (2000) 1964
2. Spring D.R. Org. Biomol. Chem. 1 (2003) 3867
3. Shang S., and Tan D.S. Curr. Opin. Chem. Biol. 9 (2005) 1
4. Arya P., Quevillon S., Joseph R., Wei C.-Q., Gan Z., Parisien M., Sesmilo B., Reddy P.T., Chen Z.-X., Durieux P., Laforce D., Campeau L.C., Khadem S., Daroszewska M., and Barnes M.L. Pure Appl. Chem. 77 (2005) 163
5. Kubota H., Lim J., Depew K.M., and Schreiber S.L. Chem. Biol. 9 (2002) 265
6. Hotha S., and Tripathi A. J. Comb. Chem. 7 (2005) 968
7. Collins P., and Ferrier R. Monosaccharides: their Chemistry and their Roles in Natural Products (1995), Wiley, Chichester, UK
8. Ferrier R.J., and Prasad N. J. Chem. Soc. C (1969) 570
9. Holder N. Chem. Rev. 82 (1982) 287
10. Liu Z.J., Zhou M., Min J.M., and Zhang L.H. Tetrahedron: Asymmetry 10 (1999) 2119
11. Brito T.M., Silva L.P., Siqueira V.L., and Srivastava R.M. J. Carbohydr. Chem. 18 (1999) 609
12. Srivastava R.M., Oliveira F.J.S., Silva L.P., Filho J.R.F., Oliveira S.P., and Lima V.L.M. Carbohydr. Res. 332 (2001) 335
13. Danishefsky S.J., and Bilodeau M.T. Angew. Chem., Int. Ed. 35 (1996) 1380
14. Fraser-Reid B. Acc. Chem. Res. 18 (1985) 347
15. Ferrier R.J. Adv. Carbohydr. Chem. Biochem. (1969) 199
16. Ramnauth J., Poulin O., Rakhit S.P., and Maddaford S.P. Org. Lett. 3 (2001) 2013
17. Tolstikov A.G., and Tolstikov G.A. Russ. Chem. Rev. 62 (1993) 579
18. Dorgan B.J., and Jackson R.F.W. Synlett (1996) 859
19. Chambers D.J., Evans G.R., and Fairbanks A.J. Tetrahedron: Asymmetry 16 (2005) 45
20. Seeberger P.H., Bilodeau M.T., and Danishefsky S.J. Aldrichimica Acta 30 (1997) 75
21. Danishefsky S.J., and Bilodeau M.T. Angew. Chem., Int. Ed. 120 (1996) 13515
22. Schmidt R.R., and Angerbauer R. Angew. Chem., Int. Ed. Engl. 16 (1977) 783
23. Williams N.R., and Wander J.D. The Carbohydrates in Chemistry and Biochemistry (1980), Academic, New York, NY p 761
24. Bracherro M.P., Cabrera E.F., Gomez G.M., and Peredes L.M.R. Carbohydr. Res. 308 (1998) 181
25. Schmidt R.R., and Angerbauer R. Carbohydr. Res. 72 (1979) 272
26. Domon D., Fujiwara K., Ohtaniuchi Y., Takezawa A., Takeda S., Kawaski H., Murai A., Kawai H., and Suzuki T. Tetrahedron Lett. 46 (2005) 8279
27. Reddy B.G., and Vankar Y.D. Tetrahedron Lett. 44 (2003) 4765
28. Lewis A., Stefanuti I., Swain S.A., Smith S.A., and Taylor R.J.K. Tetrahedron Lett. 42 (2001) 5549
29. Patterson I., and Keown L.E. Tetrahedron Lett. 38 (1997) 5727
30. Descotes G., and Martin J.C. Carbohydr. Res. 56 (1977) 168
31. Klaffke W., Pudlo P., Springer D., and Thieme J. Liebigs Ann. Chem. (1991) 509
32. Grynkiewicz G., Priebe W., and Zamojski A. Carbohydr. Res. 68 (1979) 33
33. Masson C., Soto J., and Bessodes M. Synlett (2000) 1281
34. Tilve R.D., Alexander M.V., Khandekar A.C., Samant S.D., and Kanetkar V.R. J. Mol. Catal. A: Chem. 223 (2004) 237
35. Yadav J.S., Reddy B.V.S., Murthy C.V.S.R., and Kumar G.M. Synlett (2000) 1450
36. Babu B.S., and Balasubramanian K.K. Tetrahedron Lett. 41 (2000) 1271
37. Shanmugasundaram B., Bose A.K., and Balasubramanian K.K. Tetrahedron Lett. 43 (2002) 6795
38. Ronaldo N.O., Filho J.R.F., and Srivastava R.M. Tetrahedron Lett. 43 (2002) 2141
39. Swamy N.R., and Venkateswarlu Y. Synthesis (2002) 598
40. Yadav J.S., Reddy B.V.S., and Reddy J.S.S. J. Chem. Soc., Perkin Trans. 1 (2002) 2390
41. Yadav J.S., Reddy B.V.S., Reddy K.B., and Satyanarayana M. Tetrahedron Lett. 43 (2002) 7009
42. Bettadaiah B.K., and Srinivas P. Tetrahedron Lett. 44 (2003) 7257
43. Toshima K., Ishizuka T., Matsuo G., Nakata M., and Konoshita M. J. Chem. Soc., Chem. Commun. (1993) 704
44. Lopez J.C., Gomez A.M., Valverde S., and Fraser-Reid B. J. Org. Chem. 60 (1995) 3851
45. Rafiee E., Tangestaninejad S., Habibi M.H., and Mirkhani V. Bioorg. Med. Chem. Lett. 14 (2004) 3611
46. Koreeda M., Houston T.A., Shull B.K., Klemke E., and Tuinman R.J. Synlett (1995) 90
47. Yadav J.S., Reddy B.V.S., and Pandey S.K. New J. Chem. 25 (2001) 538
48. Pachamuthu K., and Vankar Y.D. J. Org. Chem. 66 (2001) 7511
49. Agarwal A., Rani S., and Vankar Y.D. J. Org. Chem. 69 (2004) 6137
50. Banik B.K., Adler D., Nguyen P., and Srivastava N. Heterocycles 61 (2003) 101
51. Naik P.U., Nara S.J., Harjani J.R., and Salunkhe M.M. J. Mol. Catal. A: Chem. 234 (2005) 35
52. Hotha S., and Tripathi A. Tetrahedron Lett. 46 (2005) 4555
53. Kim H., Men H., and Lee C. J. Am. Chem. Soc. 126 (2004) 1336
54. Li L., Zhu L., Zhang X., Zhang G., and Qu G. Can. J. Chem. 83 (2005) 1120
55. Zhang X., Li L., and Zhang G. Green Chem. 5 (2003) 646
56. Fe2 (SO4)3 ṡ x H2 O Fe (III) % ÷ 55.8).
57. Herscovici J., Montserret R., and Antonakis K. Carbohydr. Res. 176 (1998) 219
58. Lesueur C., Nouguier R., Bertrand M.P., Hoffmann P., and De Mesmaeker A. Tetrahedron 50 (1994) 5369
59. Kashyap S., and Hotha S. Tetrahedron Lett. 47 (2006) 2021