Scope and limitations of 2-deoxy- and 2,6-dideoxyglycosyl bromides as donors for the synthesis of β-2-deoxy- and β-2,6-dideoxyglycosides

Organic Letters

Volumn 16, Issue 10, 2014, Pages 2776-2779

  Kaneko, Miho ^a   Herzon, Seth B ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; BROMINATED HYDROCARBON; GLYCOSIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; ELECTRON; GLYCOSYLATION; STEREOISOMERISM; SYNTHESIS;

AZIDES; COMBINATORIAL CHEMISTRY TECHNIQUES; ELECTRONS; GLYCOSIDES; GLYCOSYLATION; HYDROCARBONS, BROMINATED; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84900869762     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol501101f     Document Type: Article

References (62)

1. Thiem, J.; Klaffke, W. Syntheses of Deoxy Oligosaccharides. In Carbohydrate Chemistry; Springer: Berlin, Heidelberg, 1990; Vol. 154, pp 285-332.
2. Marzabadi, C. H.; Franck, R. W. Tetrahedron 2000, 56, 8385
3. Thiem, J.; Klaffke, W. Synthesis of 2-Deoxy Glycosides. In Comprehensive Glycoscience; Kamerling, H., Ed.; Elsevier: Oxford, 2007; pp 313-333.
4. Hou, D.; Lowary, T. L. Carbohydr. Res. 2009, 344, 1911
5. Borovika, A.; Nagorny, P. J. Carbohydr. Chem. 2012, 31, 255
6. Li, X.; Zhu, J. J. Carbohydr. Chem. 2012, 31, 284
7. Lairson, L. L.; Henrissat, B.; Davies, G. J.; Withers, S. G. Annu. Rev. Biochem. 2008, 77, 521
8. Hashimoto, S.-i.; Sano, A.; Sakamoto, H.; Hakajima, M.; Yanagiya, Y.; Ikegami, S. Synlett 1995, 1271
9. Guo, Y.; Sulikowski, G. A. J. Am. Chem. Soc. 1998, 120, 1392
10. Pongdee, R.; Wu, B.; Sulikowski, G. A. Org. Lett. 2001, 3, 3523
11. Tanaka, H.; Yoshizawa, A.; Takahashi, T. Angew. Chem., Int. Ed. 2007, 46, 2505
12. Issa, J. P.; Bennett, C. S. J. Am. Chem. Soc. 2014, 136, 5740
13. Lam, S. N.; Gervay-Hague, J. Org. Lett. 2003, 5, 4219
14. Issa, J. P.; Lloyd, D.; Steliotes, E.; Bennett, C. S. Org. Lett. 2013, 15, 4170
15. Thiem, J.; Gerken, M. J. Carbohydr. Chem. 1982, 1, 229
16. Thiem, J.; Gerken, M. J. Org. Chem. 1985, 50, 954
17. Nicolaou, K. C.; Ladduwahetty, T.; Randall, J. L.; Chucholowski, A. J. Am. Chem. Soc. 1986, 108, 2466
18. Ito, Y.; Ogawa, T. Tetrahedron Lett. 1987, 28, 2723
19. Thiem, J.; Schöttmer, B. Angew. Chem., Int. Ed. 1987, 26, 555
20. Preuss, R.; Schmidt, R. R. Synthesis 1988, 694
21. Perez, M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 75
22. Trumtel, M.; Tavecchia, P.; Veyrières, A.; Sinaÿ, P. Carbohydr. Res. 1989, 191, 29
23. Zuurmond, H. M.; van der Klein, P. A. M.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1992, 33, 2063
24. Castro-Palomino, J. C.; Schmidt, R. R. Synlett 1998, 501
25. Roush, W. R.; Bennett, C. E. J. Am. Chem. Soc. 1999, 121, 3541
26. Shi, L.; Kim, Y.-J.; Gin, D. Y. J. Am. Chem. Soc. 2001, 123, 6939
27. Blanchard, N.; Roush, W. R. Org. Lett. 2002, 5, 81
28. Yu, B.; Wang, P. Org. Lett. 2002, 4, 1919
29. Arnés, X.; Díaz, Y.; Castillón, S. Synlett 2003, 2143
30. Bucher, C.; Gilmour, R. Angew. Chem., Int. Ed. 2010, 49, 8724
31. Gervay, J.; Danishefsky, S. J. Org. Chem. 1991, 56, 5448
32. Yasomanee, J. P.; Demchenko, A. V. J. Am. Chem. Soc. 2012, 134, 20097
33. Kim, K. S.; Park, J.; Lee, Y. J.; Seo, Y. S. Angew. Chem., Int. Ed. 2003, 42, 459
34. Fukase, K.; Tanaka, S.-i.; Takashina, M.; Tokimoto, H.; Fujimoto, Y.; Tanaka, K. Synlett 2005, 2325
35. Okada, Y.; Nagata, O.; Taira, M.; Yamada, H. Org. Lett. 2007, 9, 2755
36. Pedersen, C. M.; Nordstrøm, L. U.; Bols, M. J. Am. Chem. Soc. 2007, 129, 9222
37. Pedersen, C. M.; Marinescu, L. G.; Bols, M. C. R. Chim. 2011, 14, 17
38. Zhou, M.; O'Doherty, G. A. Org. Lett. 2006, 8, 4339
39. Baryal, K. N.; Adhikari, S.; Zhu, J. J. Org. Chem. 2013, 78, 12469
40. Morris, W. J.; Shair, M. D. Org. Lett. 2008, 11, 9
41. Zhu, D.; Baryal, K. N.; Adhikari, S.; Zhu, J. J. Am. Chem. Soc. 2014, 136, 3172
42. Box, V. G. S. Heterocycles 1982, 19, 1939
43. Schmidt, R. R.; Michel, J. Tetrahedron Lett. 1984, 25, 821
44. Schmidt, R. R. Angew. Chem., Int. Ed. 1986, 25, 212
45. Klotz, W.; Schmidt, R. R. Liebigs Ann. Chem. 1993, 683
46. Kahne, D.; Yang, D.; Lim, J. J.; Miller, R.; Paguaga, E. J. Am. Chem. Soc. 1988, 110, 8716
47. Crich, D.; Sun, S.; Brunckova, J. J. Org. Chem. 1996, 61, 605
48. Koenigs, W.; Knorr, E. Ber. Dtsch. Chem. Ges. 1901, 34, 957
49. For a review of glycosyl halides, see: Nitz, M.; Bundle, D. Glycosyl Halides in Oligosaccharide Synthesis. In Glycoscience: Chemistry and Chemical Biology I-III; Fraser-Reid, B.; Tatsuta, K.; Thiem, J., Eds.; Springer: Berlin, Heidelberg, 2001; pp 1497-1542.
50. Paulsen, H.; Kutschker, W.; Lockhoff, O. Chem. Ber. 1981, 114, 3233
51. Paulsen, H.; Lockhoff, O. Chem. Ber. 1981, 114, 3102
52. Paulsen, H. Angew. Chem., Int. Ed. 1982, 21, 155
53. Binkley, R. W.; Koholic, D. J. J. Org. Chem. 1989, 54, 3577
54. Binkley, R. W.; Sivik, M. R. J. Carbohydr. Chem. 1991, 10, 399
55. Paterson, I.; McLeod, M. D. Tetrahedron Lett. 1995, 36, 9065
56. Zhang, Z.; Magnusson, G. J. Org. Chem. 1996, 61, 2383
57. Crimmins, M. T.; Long, A. Org. Lett. 2005, 7, 4157
58. Koeller, K. M.; Wong, C.-H. Chem. Rev. 2000, 100, 4465
59. Fraser-Reid, B.; Lopez, J. C. Armed-Disarmed Effects in Carbohydrate Chemistry: History, Synthetic and Mechanistic Studies. In Reactivity Tuning in Oligosaccharide Assembly; Fraser-Reid, B.; Lopez, J. C., Eds.; Springer: 2011; Vol. 301, pp 1-29.
60. Thiem, J.; Meyer, B. Chem. Ber. 1980, 113, 3075
61. Gillard, J. W.; Israel, M. Tetrahedron Lett. 1981, 22, 513
62. Participation of C-3 ester substituents has been reported. For a review, see: Kim, K. S.; Suk, D. H. Top. Curr. Chem. 2011, 301, 109