Traceless Staudinger ligation of glycosyl azides with triaryl phosphines: Stereoselective synthesis of glycosyl amides

Journal of Organic Chemistry

Volumn 71, Issue 12, 2006, Pages 4565-4577

  Bianchi, Aldo ^a   Bernardi, Anna ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSYL AMIDES; PYRANOSE CONFORMATION; STEREOSELECTIVE SYNTHESIS;

CATALYSIS; ESTERS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS; SUGARS;

NITROGEN COMPOUNDS;

ALPHA GLYCOSYL AMIDE; AMIDE; APROTIC SOLVENT; AZIDE; BENZENE DERIVATIVE; BENZYL ETHER; DIPHENYLPHOSPHANYL PHENYL ESTER; ESTER; ETHER; FUCOSE; GALACTOSE; GLUCOSE; GLYCOSIDE; GLYCOSYL AZIDE; MONOSACCHARIDE; O BENZYL ALPHA GLYCOSYL AZIDE; PHENOL; PHOSPHINE DERIVATIVE; SOLVENT; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONFORMATION; DEPROTECTION REACTION; EPIMERIZATION; HYDROGENATION; LIGATION; METABOLITE; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REDUCTION; STAUDINGER LIGATION; STEREOCHEMISTRY; SYNTHESIS;

AMIDES; AZIDES; CARBOHYDRATE CONFORMATION; GLYCOSIDES; PHOSPHINES; STEREOISOMERISM;

EID: 33744911085     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060409s     Document Type: Article

References (65)

1. Neo-glycoconjugates, part B: biomedical applications. Methods in Enzymology; Lee, Y., Lee, R., Abelson, J., Simon, M., Eds.; Academic Press: New York, 1995; Vol. 247.
2. One example of α-linked glycopeptide has been described: Shibata, S.; Takeda, T.; Natori, Y. J. Biol. Chem. 1988, 263, 12843-12845.
3. Bosques, C. J.; Tschampel, S. M.; Woods, R.; Imperiali, B. J. Am. Chem. Soc. 2004, 126, 8421-8425.
4. Hackenberger, C. P. R.; O'Reilly, M. K.; Imperiali, B. J. Org. Chem. 2005, 70, 3574-3578.
5. Sridhar, P. R.; Prabhu, K. R.; Chandrasekaran, S. J. Org. Chem. 2003, 68, 5261-5264.
6. Matsuo, I.; Nakahara, Y.; Ito, Y.; Nukada, T.; Nakahara, T.; Ogawa, T. Bioorg. Med. Chem. 1995, 3, 1455-1463.
7. Saha, U. K.; Roy, R. Tetrahedron Lett. 1995, 36, 3635-3638.
8. Sabesan, S. Tetrahedron Lett. 1997, 38, 3127-3130.
9. Inazu, T.; Kobayashi, K. Synlett 1993, 869-870.
10. Bosch, I.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671-4674.
11. Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97-106.
12. Malkinson, J. P.; Falconer, R. A.; Toth, I. J. Org. Chem. 2000, 65, 5249-5252.
13. Shangguan, N.; Katukojvala, S.; Greenberg, R.; Williams, L. J. J. Am. Chem. Soc. 2003, 125, 7754-7755.
14. (a) Staudinser, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635-646.
15. (b) Gololobov, Y. G.; Kasukhin, L. F. Tetrahedron 1992, 48, 1353-1407.
16. Kovács, L.; Ösz, E.; Domokos, V.; Holzer, W.; Györgydeák, Z. Tetrahedron 2001, 57, 4609-4621.
17. Ratcliffe, A. J.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans. 1 1989, 1805-1810.
18. Ratcliffe, A. J.; Konradsson, P.; Fraser-Reid, B. J. Carbohydr. Res. 1991, 216, 323-335.
19. Damkaci, F.; DeShong, P. J. Am. Chem. Soc. 2003, 125, 4408-4409.
20. Bianchi A. PhD Thesis, Universita' di Milano, 2004-2005.
21. (a) Bianchi, A.; Bernardi, A. Tetrahedron Lett. 2004, 45, 2231-2234.
22. (b) Bianchi, A.; Russo, A.; Bernardi, A. Tetrahedron: Asymmetry 2005, 16, 381-386.
23. (a) Saxon, E.; Bertozzi, C. R. Science 2000, 287, 2007-2010.
24. (b) Saxon, E.; Armstrong, J. I.; Bertozzi, C. R. Org. Lett. 2000, 2, 2141-2143.
25. Nillson, B. L.; Kiessling, L. L.; Raines, R. T. Org. Lett. 2000, 2, 1939-1941.
26. Koehn, M.; Breinbauer, R. Angew. Chem., Int. Ed. 2004, 43, 3106-3116 and referencs therein.
27. He, Y.; Hinklin, R. J.; Chang, J.; Kiessling, L. L. Org. Lett. 2004, 6, 4479-4482.
28. Lin, F. L.; Hoyt, H. M.; van Halbeek, H.; Bergman, R. G.; Bertozzi, C. J. Am. Chem. Soc. 2005, 127, 2686-2695.
29. (a) Ogawa, T.; Nakabayashi, S.; Shibata, S. Agric. Biol. Chem. 1983, 47, 281-285.
30. (b) Sabesan, S.; Neira, S. Carbohydr. Res, 1992, 223, 169-185.
31. (a) Paulsen H. Adv. Carbohydr. Chem. 1971, 26, 127.
32. (b) Györgydeák, Z.; Szilágyi, L.; Paulsen H. J. Carbohydr. Chem. 1993, 12, 139-163.
33. Szylágyi, L.; Györgydeák, Z. Carbohydr. Res. 1985, 143, 21-41.
34. 2,3,4,6-tetra-O-acetyl-β-D-glucosyl chloride: Korytnyk, W.; Mills J. A. J. Chem. Soc. 1959, 636-649.
35. 3,4,6-tri-O-acetyl-2-N-acetyl-2-deoxy-α-D-glucopyranosyl chloride: Martichonok, V.; Whitesides, G. M. J. Org. Chem. 1996, 61, 1702-1706.
36. 2-N-phthalimido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl bromide: Baluja, G.; Chase, B. H.; Kenner, G. W.; Todd, A. J. Chem. Soc. 1960, 4678-4681.
37. Tropper, F. D.; Andersson, F. O.; Braun, S.; Roy, R. Synthesis 1992, 618-620.
38. Soli, E. D.; Manoso, A. S.; Patterson, M. C.; DeShong, P. J. Org. Chem. 1999, 64, 3171-3177.
39. (a) Gervay, J.; Nguyen, T. N.; Hadd, M. J. Carbohydr. Res. 1997, 300, 119-125.
40. (b) Hadd, M. J.; Gervay, J. Carbohydr. Res. 1999, 320, 61-69.
41. Rauchfuss, T. B. Inorg. Chem. 1977, 16, 2966-2968.
42. Herzner, H.; Reipen, T.; Schulte, M.; Kunz, H. Chem. Rev. 2000, 100, 4495-4537.
43. (a) Inazu, T.; Kobayashi, K. Synlett 1993, 869-870.
44. (b) Bosch, I.; Romea, P.; Urpi, F.; Vilarrasa, J. Tetrahedron Lett. 1993, 34, 4671-4674.
45. (a) Kovács, L.; Pintér, I.; Messmer, A. Carbohydr. Res. 1985, 141, 57-65.
46. (b) Kovács, L.; Pintér, I.; Messmer, A. Carbohydr. Res. 1987, 166, 101-111.
47. Johnson, A. W. Ylides and Imines of Phosphorus; Wiley: New York, 1993.
48. Tachibana, Y.; Matsubara, N.; Nakajima, F.; Tsuda, T.; Tsuda, S.; Monde, K.; Nishimura, S. I. Tetrahedron 2002, 58, 10213-10224.
49. Gololobov, Y. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437-472.
50. (a) Widauer, C.; Grützmacher, H.; Shevchenko, I.; Gramlich, V. Eur. J. Inorg. Chem. 1999, 1659-1664 and references therein.
51. (b) Alajarín, M.; Conesa, C.; Rzepa, H. S. J. Chem. Soc., Perkin Trans. 2 1999, 1811-1814.
52. (c) Tian, W. Q.; Wang, Y. A. J. Org. Chem. 2004, 69, 4299-4308.
53. (c) Zhang, S.; Wang, Y. A. J. Chem. Theory Comput. 2005, 1, 353-362.
54. (a) Molina, P.; López-Leonardo, C.; Llamas-Botía, J.; Foces-Foces, C.; Fernández-Castaño, C. Tetrahedron 1996, 52, 9629-9642.
55. (b) Alajarín, M.; Molina, P.; López-Lazaro, A.; Foces-Foces, C. Angew. Chem., Int. Ed. 1997, 36, 67-70.
56. (a) Hillhouse, G. L.; Goeden, G. V.; Haymore, B. L. Inorg. Chem. 1982, 21, 2064.
57. (b) Chernega, A. N.; Antipin, M. Y.; Struchkov, Y. T.; Boldeskul, I. E.; Ponomarchuk, M. P.; Kasukhin, L. F.; Kukhar, V. P. Zh. Obshch. Khim. 1984, 54, 1979.
58. (c) Chidester, C. G.; Szmuszkovicz, J.; Duchamp, D. J.; Laurian, L. G.; Freeman, J. P. Acta Crystallogr., Sect. C 1988, 44, 1080.
59. (d) Chernega, A. N.; Antipin, M. Y.; Struchkov, Y. T.; Ponomarchuk, M. P.; Kasukhin, L. F.; Kukhar, V. P. Zh. Obshch. Khim. 1989, 59, 1256.
60. (e) Tolmachev, A. A.; Kostyuk, A. N.; Kozlov, E. S.; Polishchuk, A. P.; Chernega, A. N. Zh. Obshch. Khim. 1992, 62, 2675.
61. (f) Goerlich, J. R.; Farkens, M.; Fischer, A.; Jones, P.; Schmutzler, R. Z. Anorg. Allg. Chem. 1994, 620, 707.
62. (g) Bieger, K.; Bouhadir, G.; Reau, R.; Dahan, F.; Bertrand, G. J. Am. Chem. Soc. 1994, 118, 8087-8094.
63. (a) Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 5583-5584.
64. (b) Ottoson, H.; Udodong, U.; Wu, Z.; Fraser-Reid, B. J. Org. Chem. 1990, 55, 6068-6070.
65. Grandjean, C.; Boutonnier, A.; Guerreiro, C.; Fournier, J.-M.; Mulard, L. A. J. Org. Chem. 2005, 70, 7123-7132.