Sequential directed epoxydation-acidolysis from glycals with MCPBA. A flexible approach to protected glycosyl donors

Journal of Organic Chemistry

Volumn 76, Issue 23, 2011, Pages 9622-9629

  Marín, Irene ^a   Castilla, Javier ^a   Matheu, M Isabel ^a   Díaz, Yolanda ^a   Castillón, Sergio ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CHLOROBENZOATES; FULLY PROTECTED; GLYCALS; GLYCOSYL DONORS; HYDROXYL GROUPS; RING OPENING;

EPOXIDATION;

SYNTHESIS (CHEMICAL);

3 CHLOROBENZOIC ACID; DISACCHARIDE; GLUCONATE CALCIUM;

ARTICLE; EPOXIDATION; GLYCOSYLATION; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

CHLOROBENZOATES; GLYCOSIDES; MOLECULAR CONFORMATION; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 82255179796     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201165v     Document Type: Article

References (57)

1. Stallforth, P.; Lepenies, B.; Adikebian, A.; Seeberger, P. H. J. Med. Chem. 2009, 52, 5561-5577
2. Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380-1419
3. Somsak, L. Chem. Rev. 2001, 101, 81-135
4. Gómez, A.; López, J. C. Carbohydr. Chem. 2009, 35, 289-309
5. Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661-6666
6. Gordon, D. M.; Danishefsky, S. J. Carbohydr. Res. 1990, 206, 361-366
7. Seeberger, P. H.; Eckhardt, M.; Gutteridge, C. E.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10064-10072
8. Demchenko, A. V.; Pornsuriyasak, P.; De Meo, C.; Malysheva, N. N. Angew. Chem., Int. Ed. 2004, 43, 3069-3072
9. Li, Y.; Tang, P.; Chen, Y.; Yu, B. J. Org. Chem. 2008, 73, 4323-4325
10. Gordon, D.; Danishefsky, S. J. Carbohyd. Res. 1990, 206, 361-366
11. Plante, O. J.; Andrade, R. B.; Seeberger, P. H. Org. Lett. 1999, 1, 211-214
12. Plante, O. J.; Palmacci, E. R.; Andrade, R. B.; Seeberger, P. H. J. Am. Chem. Soc. 2001, 123, 9545-95554
13. Cheshev, P.; Marra, A.; Dondoni, A. Carbohydr. Res. 2006, 341, 2714-2716
14. Bellucci, G.; Catelani, G.; Chiappe, C.; D'Andrea, F. Tetrahedron Lett. 1994, 35, 8433-8436
15. Cavicchioli, M.; Mele, A.; Montanari, V.; Resnati, G. J. Chem. Soc., Chem. Commun. 1995, 901-902
16. Honda, E.; Gin, D. Y. J. Am. Chem. Soc. 2002, 124, 7343-7352
17. Liu, C.-J.; Yu, W.-Y.; Li, S.-G.; Che, C.-M. J. Org. Chem. 1998, 63, 7364
18. Yu, X.-Q.; Huang, J.-S.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2000, 122, 5337
19. Soldaini, G.; Cardona, F.; Goti, A. Tetrahedron Lett. 2003, 44, 5589-5592
20. Soldaini, G.; Cardona, F.; Goti, A. Org. Lett. 2005, 7, 725-728
21. Goti, A.; Cardona, F.; Soldaini, G.; Crestini, C.; Fiani, C.; Saladino, R. Adv. Synth. Catal. 2006, 348, 476-486
22. Saladino, R.; Crestini, C.; Crucianelli, M.; Soldaini, G.; Cardona, F.; Goti, A. J Mol. Catal. A 2008, 284, 108-115
23. Boyd, E. C.; Jones, R. V. H.; Quayle, P.; Waring, A. J. Green Chem. 2003, 5, 679-681
24. Levecque, P.; Gammon, D. W.; Kinfe, H. H.; Jacobs, P.; De Vos, D.; Sels, B. Adv. Synth. Catal. 2008, 350, 1557-1568
25. Bílik, V.; Kučár, Š. Carbohydr. Res. 1970, 13, 311-313
26. Marín, I.; Matheu, M. I.; Díaz, Y.; Castillón, S. Adv. Synth. Catal 2010, 352, 3407-3418
27. Lichtenthaler, F. W.; Schneider-Adams, T. J. Org. Chem. 1994, 59, 6728-6734
28. Broder, W.; Kunz, H. Carbohydr. Res. 1993, 249, 221-241
29. Schmidt, R. R.; Effenberger, G. Carbohydr. Res. 1987, 171, 59-79
30. Wu, E.; Wu, Q. Carbohydr. Res. 1993, 250, 327-333
31. Lemieux, R. U.; Morgan, A. R. Can. J. Chem. 1965, 43, 2199-2204
32. Sanders, W. J.; Kiessling, L. L. Tetrahedron Lett. 1994, 35, 7335-7338
33. Charette, A. B.; Marcoux, J.-F.; Cote, B. Tetrahedron Lett. 1991, 32, 7215-7218
34. Tiwari, P.; Misra, A. K. J. Org. Chem. 2006, 71, 2911-2913
35. Rani, S.; Vankar, Y. D. Tetrahedron Lett. 2003, 44, 907-909
36. Lee, H.-K.; Scanlan, C. N.; Huang, C.-Y.; Chang, A. Y; Calarese, D. A.; Dwek, R. A.; Rudd, P. M.; Burton, D. R.; Wilson, I. A.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 2004, 43, 1000-1003
37. Wong, C.-H.; Ye, X.-S.; Zhang, Z. J. Am. Chem. Soc. 1998, 120, 7137-7138
38. Zhu, T.; Booms, G.-J. Tetrahedron Asymmetry 2000, 11, 199-205
39. Reina, J. J.; Rojo, J. Tetrahedron Lett. 2006, 47, 2475-2478
40. Matsushita, Y.; Sugamoto, K.; Kita, Y.; Matsui, T. Tetrahedron Lett. 1997, 38, 8709-8712
41. Dötz, K. H.; Otto, F.; Nieger, M. J. Organomet. Chem. 2001, 621, 77-88
42. Adam, W.; Wirth, T. Acc. Chem. Res. 1999, 32, 703-710
43. Adam, W.; Bach, R. D.; Dmitrenko, O.; Saha-Möller, C. R. J. Org. Chem. 2000, 65, 6715-6728
44. Holla, E. W. Angew. Chem., Int. Ed. Engl. 1989, 28, 220-221
45. Kan, C.; Long, C. M.; Paul, M.; Ring, C. M.; Tully, S. E.; Rojas, C. M. Org. Lett. 2001, 3, 381-384
46. Toyokuni, T.; Cai, S.; Dean, B. Synthesis 1992, 1236-1238
47. Jacquinet, J.-C. Carbohydr. Res. 1990, 199, 153-181
48. Debost, J.-L.; Gelas, J.; Horton, D.; Mols, O. Carbohydr. Res. 1984, 125, 329-335
49. Kitamura, M.; Isobe, M.; Ichikawa, Y.; Goto, T. J. Am. Chem. Soc. 1984, 106, 3252-3257
50. Parker, K. A.; Georges, A. T. Org. Lett. 2000, 2, 497-499
51. Reina, J. J.; Díaz, I.; Nieto, P. M.; Campillo, N. E.; Páez, J. A.; Tabarani, G.; Fieschi, F.; Rojo, J. Org. Biomol. Chem. 2008, 6, 2743-2754
52. Compostella, F.; Ronchi, S.; Panza, L.; Mariotti, S.; Mori, L.; De Libero, G.; Ronchetti, F. Chem. - Eur. J. 2006, 12, 5587-5595
53. Obadiah, J. P.; Palmacci, E. R.; Seeberger, P. H. Org. Lett. 2000, 2, 3841-3843
54. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3 rd ed.; Pergamon Press: Oxford, 1989.
55. Namchuk, M. N.; McCarter, J. D.; Becalski, A.; Andrews, T.; Withers, S. G. J. Am. Chem. Soc. 2000, 122, 1270-1277
56. Mayer, T. G.; Kratzer, B.; Schmidt, R. R. Angew. Chem. 1994, 106, 2289-2293
57. Mahling, J.-A.; Schmidt, R. R. Synthesis 1993, 3, 325-328