Carbasugar analogues of galactofuranosides: β-O-linked derivatives and towards β-S-linked derivatives

Carbohydrate Research

Volumn 346, Issue 11, 2011, Pages 1277-1290

  Frigell, Jens ^a   Eriksson, Lars ^a   Cumpstey, Ian ^a,b  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b CNRS   (France)

Author keywords

Carbasugars; Epoxide opening; Galactofuranose; Glycomimetics; Pseudodisaccharides; Ring closing metathesis

Indexed keywords

CARBASUGARS; EPOXIDE-OPENING; GALACTOFURANOSE; GLYCOMIMETICS; PSEUDODISACCHARIDES; RING CLOSING METATHESIS;

CARBOHYDRATES; ETHERS; GLUCOSE; SULFUR;

NUCLEOPHILES;

1,2 EPOXIDE; BETA GALACTOFURANOSE; CARBASUGAR; ELECTROPHILE; GLUCOSE; LEWIS ACID; NUCLEOPHILE; SULFUR; UNCLASSIFIED DRUG;

CARBOHYDRATE METABOLISM; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CONFERENCE PAPER; CONTROLLED STUDY; CROSS COUPLING REACTION; PRIORITY JOURNAL; RING CLOSING METATHESIS;

CARBOHYDRATES; DISACCHARIDES; EPOXY COMPOUNDS; GALACTOSIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 79958081669     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2011.04.032     Document Type: Conference Paper

References (75)

1. Preliminary report: Frigell, J.; Cumpstey, I. Tetrahedron Lett. 2007, 48, 9073-9076.
2. Preliminary report: Frigell, J.; Cumpstey, I. Tetrahedron Lett. 2009, 50, 5142-5144.
3. Witczak, Z. J. In Fraser-Reid, B. O., Tatsuta, K., Thiem, J., Eds., 2nd ed.; Glycoscience; Springer: Heidelberg, 2008; pp 815-840.
4. Peltier, P.; Euzen, R.; Daniellou, R.; Nugier-Chauvin, C.; Ferrières, V. Carbohydr. Res. 2008, 343, 1897-1923.
5. Richards, M. R.; Lowary, T. L. ChemBioChem 2009, 10, 1920-1938.
6. Pedersen, L. L.; Turco, S. J. Cell. Mol. Life Sci. 2003, 60, 259-266.
7. (a) Nicotra, F.; Panza, L.; Ronchetti, F.; Russo, G.; Toma, L. Carbohydr. Res. 1987, 171, 49-58;
8. (b) Kovensky, J.; Cirelli, A. F.; Sinaÿ, P. Carbohydr. Lett. 1999, 3, 271-276;
9. (c) Kovensky, J.; McNeil, M.; Sinaÿ, P. J. Org. Chem. 1999, 64, 6202-6205;
10. (d) Kovensky, J.; Burrieza, D.; Colliou, V.; Cirelli, A. F.; Sinaÿ, P. J. Carbohydr. Chem. 2000, 19, 1-12;
11. (e) Kovensky, J.; Sinaÿ, P. Eur. J. Org. Chem. 2000, 64, 3523-3526;
12. (f) Owen, D. J.; Thomson, R. J.; von Itzstein, M. Carbohydr. Res. 2002, 337, 2017-2022;
13. (g) Caravano, A.; Mengin-Lecreulx, D.; Brondello, J.-M.; Vincent, S. P.; Sinaÿ, P. Chem. Eur. J. 2003, 9, 5888-5898;
14. (h) Cribiu, R.; Cumpstey, I. Chem. Commun. 2008, 1246-1248;
15. (i) Cribiu, R.; Borbas, K. E.; Cumpstey, I. Tetrahedron 2009, 65, 2022-2031.
16. (a) Marino, K.; Lima, C.; Maldonado, S.; Marino, C.; de Lederkremer, R. M. Carbohydr. Res. 2002, 337, 891-898;
17. (b) Davis, C. B.; Hartnell, R. D.; Madge, P. D.; Owen, D. J.; Thomson, R. J.; Chong, A. K. J.; Coppel, R. L.; von Itzstein, M. Carbohydr. Res. 2007, 342, 1773-1780;
18. (c) Lopez, G.; Daniellou, R.; O'Donohue, M.; Ferrières, V.; Nugier-Chauvin, C. Bioorg. Med. Chem. Lett. 2007, 17, 434-438;
19. (d) Repetto, E.; Marino, C.; Uhrig, L.; Varela, O. Bioorg. Med. Chem. 2009, 17, 2703-2711.
20. (a) Varela, O.; Cicero, D.; de Lederkremer, R. M. Carbohydr. Res. 1989, 54, 1884-1890;
21. (b) Randell, K. D.; Johnston, B. D.; Pinto, B. M. Carbohydr. Res. 2000, 326, 145-150;
22. (c) Randell, K. D.; Johnston, B. D.; Lee, E. E.; Pinto, B. M. Tetrahedron: Asymmetry 2000, 11, 207-222;
23. (d) Ghavami, A.; Chen, J. J.-W.; Pinto, B. M. Carbohydr. Res. 2004, 339, 401-408.
24. (a) Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yah, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733-6736;
25. (b) Lee, R. E.; Smith, M. D.; Pickering, L.; Fleet, G. W. J. Tetrahedron Lett. 1999, 40, 8689-8692;
26. (c) Liautard, V.; Christina, A. E.; Desvergnes, V.; Martin, O. R. J. Org. Chem. 2006, 71, 7337-7345;
27. (d) Liautard, V.; Desvergnes, V.; Martin, O. R. Org. Lett. 2006, 8, 1299-1302;
28. (e) Liautard, V.; Desvergnes, V.; Itoh, K.; Liu, H.-W.; Martin, O. R. J. Org. Chem. 2008, 73, 3103-3115.
29. Nisic, F.; Bernardi, A. Carbohydr. Res. 2011, 346, 465-471.
30. McCasland, G. E.; Furuta, S.; Durham, L. J. J. Org. Chem. 1966, 31, 1516-1521.
31. Arjona, O.; Gómez, A. M.; López, J. C.; Plumet, J. Chem. Rev. 2007, 107, 1919-2036.
32. Huber, R.; Vasella, A. Tetrahedron 1990, 46, 33-58.
33. Horneman, A. M.; Lundt, I. J. Org. Chem. 1998, 63, 1919-1928.
34. Horneman, A. M.; Lundt, I. Synthesis 1999, 317-325.
35. Ghosh, S.; Bhaumik, T.; Sarkar, N.; Nayek, A. J. Org. Chem. 2006, 71, 9687-9694.
36. Nguyen van Nhien, A.; Soriano, E.; Marco-Contelles, J.; Postel, D. Carbohydr. Res. 2009, 344, 1605-1611.
37. Ye, W.; He, M.; Schneller, S. W. Tetrahedron Lett. 2009, 50, 7156-7158.
38. Li, J.; Lowary, T. L. Org. Lett. 2008, 10, 881-884.
39. Frigell, J.; Cumpstey, I. Beilstein J. Org. Chem. 2010, 6, 1127-1131.
40. Frigell, J.; Pearcey, J. A.; Lowary, T. L.; Cumpstey, I. Eur. J. Org. Chem. 2011, 1367-1375.
41. Ogawa, S.; Sasaki, S.; Tsunoda, H. Carbohydr. Res. 1995, 274, 183-196.
42. Ogawa, S.; Furuya, T.; Tsunoda, H.; Hindsgaul, O.; Stangier, K.; Palcic, M. M. Carbohydr Res. 1995, 271, 197-205.
43. For a review, see: Cumpstey, I. Carbohydr. Res. 2009, 344, 2285-2310.
44. For reviews, see: (a) Madsen, R. Eur. J. Org. Chem. 2007, 399-415;
45. (b) Plumet, J.; Gómez, A. M.; López, J. C. Mini-Rev. Org. Chem. 2007, 4, 201-216.
46. Seepersaud, M.; Al-Abed, Y. Org. Lett. 1999, 1, 1463-1465.
47. Callam, C. S.; Lowary, T. L. Org. Lett. 2000, 2, 167-169.
48. Seepersaud, M.; Al-Abed, Y. Tetrahedron Lett. 2000, 41, 7801-7803.
49. Callam, C. S.; Lowary, T. L. J. Org. Chem. 2001, 66, 8961-8972.
50. Gillaizeau, I.; Charamon, S.; Agrofoglio, L. A. Tetrahedron Lett. 2001, 42, 8817-8819.
51. Lee, K.; Cass, C.; Jacobson, K. A. Org. Lett. 2001, 3, 597-599.
52. Agrofoglio, L. A.; Amblard, F.; Nolan, S. P.; Charamon, S.; Gillaizeau, I.; Zevaco, T. A.; Guenot, P. Tetrahedron 2004, 60, 8397-8404.
53. Moon, H. R.; Choi, W. J.; Kim, H. O.; Jeong, L. S. Chem. Lett. 2004, 33, 506-507.
54. Cho, J. H.; Bernard, D. L.; Sidwell, R. W.; Kern, E. R.; Chu, C. K. J. Med. Chem. 2006, 49, 1140-1148.
55. Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327-336.
56. Zhang, Y.-M.; Mallet, J.-M.; Sinay, P. Carbohydr. Res. 1992, 236, 73-88.
57. Köll, P.; John, H.-G.; Schulz, J. Liebigs Ann. Chem. 1982, 613-625.
58. (a) Cram, D. J.; Kopecky, K. R. J. Am. Chem. Soc. 1959, 81, 2748-2755;
59. (b) Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191-1223.
60. Andresen, T. L.; Skytte, D. M.; Madsen, R. Org. Biomol. Chem. 2004, 2, 2951-2957.
61. Grindley, T. B.; Cote, C. J. P.; Wickramage, C. Carbohydr. Res. 1985, 140, 215-238.
62. Sajiki, H.; Hirota, K. Tetrahedron 1998, 54, 13981-13996.
63. Bock, K.; Meldal, M.; Refn, S. Carbohydr. Res. 1991, 221, 1-16.
64. Constantino, M. G.; da Silva, G. V. J. Tetrahedron 1998, 54, 11363-11374.
65. Costantino, V.; Fattorusso, E.; Imperatore, C.; Mangoni, A. J. Org. Chem. 2008, 73, 6158-6165.
66. Marshner, C.; Baumgartner, J.; Griengl, H. J. Org. Chem. 1995, 60, 5224-5235.
67. Tadano, K.-I.; Hakuba, K.; Kimura, H.; Ogawa, S. J. Org. Chem. 1989, 54, 276-279.
68. (a) Liptak, A.; Imre, J.; Nanasi, P. Carbohydr. Res. 1981, 92, 154-156;
69. (b) Ennis, S. C.; Cumpstey, I.; Fairbanks, A. J.; Butters, T. D.; Mackeen, M.; Wormald, M. R. Tetrahedron 2002, 58, 9403-9411;
70. (c) Ruiz Contreras, R.; Kamerling, J. P.; Vliegenthart, J. F. G. Recl. Trav. Chim. Pays-Bas 1991, 110, 85-88.
71. Goueth, P. Y.; Ronco, G.; Villa, P. J. Carbohydr. Chem. 1994, 13, 679-696.
72. Ogawa, S.; Sasaki, S.-I.; Tsunoda, H. Chem. Lett. 1993, 1587-1590.
73. Ogawa, S.; Hirai, K.; Odagiri, T.; Matsunaga, N.; Yamazaki, T.; Nakajima, A. Eur. J. Org. Chem. 1998, 1099-1109.
74. Guidot, J.-P.; le Gall, T. Tetrahedron Lett. 1993, 34, 4647.
75. Ahn, Y.-M.; Yang, K.; Georg, G.-I. Org. Lett. 2001, 3, 1411-1413.