Reaction of 1,2-orthoesters with HF-pyridine: A method for the preparation of partly unprotected glycosyl fluorides and their use in saccharide synthesis

Organic Letters

Volumn 11, Issue 18, 2009, Pages 4128-4131

  Cristobal Lopez J ^a   Ventura, Juan ^a   Uriel, Clara ^a   Gómez, Ana M ^a   Fraser Reld, Bert ^b  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b Natural Products and Glycotechnology Research Institute Inc NPG   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE; FLUORIDE; HYDROFLUORIC ACID; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

CARBOHYDRATES; FLUORIDES; HYDROFLUORIC ACID; MOLECULAR STRUCTURE; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 70349114277     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901630d     Document Type: Article

References (69)

1. (a) Varki, A. Glycobiology 1993, 3, 97-130.
2. (b) Reuter, G.; Gabius, H. J. Mol. Life Sci. 1999, 55, 368-422.
3. Burton, D. R.; Dwek, R. A. Science 2006, 313, 627-628.
4. (c) McReynolds, K. D.; Gervay-Hague, J. Chem. Rev. 2007, 107, 1533-1552.
5. Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503-1531.
6. (a) Boons, G.-J. Tetrahedron 1996, 52, 1095-1121.
7. (b) Demchenko, A. V. Lett. Org. Chem. 2005, 2, 580-589.
8. (c) Zhu, X.; Schmidt, R. R. Angew. Chem., Int. Ed. 2009, 48, 1900-1934.
9. Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823-938.
10. Baeschlin, D. K.; Green, L. G.; Hahn, M. G.; Hinzen, B.; Ince, S. J.; Ley, S. V. Tetrahedron: Asymmetry 2000, 11, 173-197.
11. Litjens, R. E. J. N.; van den Bos, L. J.; Codée, J. D. C.; Overkleeft, H. S.; van der Marel, G. A. Carbohydr. Res. 2007, 342, 419-429.
12. Fraser-Reid, B.; López, J. C.; Gómez, A. M.; Uriel, C. Eur. J. Org. Chem. 2004, 1387-1395.
13. (a) Boons, G.-J.; Zhu, T. Synlett 1997, 809-811.
14. (b) Matsuo, I.; Isomura, M.; Miyazaki, T.; Sakakibara, T.; Ajisaka, K. Carbohydr. Res. 1998, 305, 401-413.
15. (c) Plante, O. J.; Palmacci, E. R.; Andrade, R. B.; Seeberger, P. H. J. Am. Chem. Soc. 2001, 123, 9545-9554.
16. (d) López, J. C.; Agocs, A.; Uriel, C.; Gómez, A. M.; Fraser-Reid, B. Chem. Commun. 2005, 5088-5090.
17. (a) Kanie, O.; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 12073-12074.
18. (b) Demchenko, A. V.; Pornsuriyasak, P.; De Meo, C.; Malysheva, N. N. Angew. Chem., Int. Ed. 2004, 43, 3069-3072.
19. (c) Pornsuriyasak, P.; Demchenko, A. V. Chem.-Eur. J. 2006, 12, 6630-6646.
20. (d) Kaeothip, S.; Pornsuriyasak, P.; Rath, N. P.; Demchenko, A. V. Org. Lett. 2009, 11, 799-802.
21. (a) Demchenko, A. V.; De Meo, C. Tetrahedron Lett. 2002, 43, 8819-8822.
22. (b) López, J. C.; Uriel, C.; Guillamón-Martin, A.; Valverde, S.; Gómez, A. M. Org. Lett. 2007, 9, 2759-2762.
23. (a) Zhu, T.; Boons, G. J. Tetrahedron Lett. 1998, 39, 2187-2190.
24. (b) Zhu, T.; Boons, G. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1898-2000.
25. Hanessian, S.; Lu, P. P.; Ishida, H. J. Am. Chem. Soc. 1998, 120, 13296-13330.
26. (a) Kochetkov, N. K.; Khorlin, A. J.; Bochkov, A. F. Tetrahedron Lett. 1964, 5, 289-293.
27. (b) Kochetkov, N. K. Tetrahedron 1987, 43, 2389-2436.
28. Fraser-Reid, B.; López, J. C. Orthoesters and Related Derivatives. In Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance; Demchenko, A. V., Ed.; Wiley-VCH: New York, 2008; Chapter 5.1.
29. Kong, F. F. Carbohydr. Res. 2007, 342, 345-373.
30. (a) Allen, J. G.; Fraser-Reid, B. J. Am. Chem. Soc. 1999, 121, 468-469.
31. (b) Mach, M. Schlueter, U.; Mathew, F.; Fraser-Reid, B.; Hazen, K. C. Tetrahedron 2002, 58, 7345-7354.
32. (c) Lu, J.; Jayaprakash, K. N.; Schlueter, U.; Fraser-Reid, B. J. Am. Chem. Soc. 2004, 126, 7450-7457.
33. (d) Lu, J.; Fraser-Reid, B. Chem. Commun. 2005, 862-864.
34. (e) Jayaprakash, K. N.; Lu, J.; Fraser-Reid, B. Angew. Chem., Int. Ed. 2005, 44, 5894-5898.
35. Fraser-Reid, B.; Lu, J.; Jayaprakash, K. N.; López, J. C. Tetrahedron: Asymmetry 2006, 17, 2449-2463.
36. (a) Bamhaoud, T.; Sanchez, S.; Prandi, J. Chem. Commun. 2000, 659-660.
37. (b) Sanchez, S.; Bamhaoud, T.; Prandi, J. Tetrahedron Lett. 2000, 41, 7447-7452.
38. (c) Marotte, K.; Sanchez, S.; Bamhaoud, T.; Prandi, J. Eur. J. Org. Chem. 2003, 3587-3598.
39. (a) Liu, X.; Wada, R.; Boonyarattanakalin, S.; Castagner, B.; Seeberger, P. H. Chem. Commun. 2008, 3510-3512.
40. (b) Boonyarattanakalin, S.; Liu, X.; Michieletti, M.; Lepenies, B.; Seeberger, P. H. J. Am. Chem. Soc. 2008, 130, 16791-16799.
41. (c) Ravidà, A.; Liu, X.; Kovacs, L.; Seeberger, P. H. Org. Lett. 2006, 8, 1815-1818.
42. Fraser-Reid, B.; Udodong, U. E.; Wu, Z.; Ottosson, H.; Merrit, J. R.; Rao, C. S.; Roberts, C.; Madsen, R. Synlett 1992, 927-942.
43. Oscarson, S. Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinaÿ, P., Eds.; Wiley-VCH: Weinheim, 2000; Vol.1, pp 93-116.
44. Mukaiyama, T. Angew. Chem., Int. Ed. 2004, 43, 5590-5614.
45. Barluenga, J.; González, J. M.; Campos, P. J.; Asensio, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 319-320.
46. López, J. C.; Bernal-Albert, P.; Uriel, C.; Valverde, S.; Gómez, A. M. J. Org. Chem. 2007, 72, 10268-10271.
47. López, J. C.; Bernal-Albert, P.; Uriel, C.; Gómez, A. M. Eur. J. Org. Chem. 2008, 5037-5041.
48. Olah, G. A.; Welch, J. T.; Vankar, Y. D.; Nojima, M.; Kerekes, I.; Olah, J. A. J. Org. Chem. 1979, 44, 3872-3881.
49. The HF-pyridine complex has been used as a source of fluoride in the preparation of glycosyl fluorides :(a) Hayashi, M.; Hashimoto, S.; Noyori, R. Chem. Lett. 1984, 1747-1750.
50. (b) Szarek, W. A.; Grynkiewicz, G.; Doboszewski, B.; Hay, G. W. Chem. Lett. 1984, 1751-1754.
51. (c) Bröder, W.; Kunz, H. Carbohydr. 1993, 249, 221-241.
52. (d) Palme, M.; Vasella, A. Helv. Chim. Acta 1995, 78, 959-969.
53. (e) Lee, Y. J.; Lee, B. Y.; Jeon, H. B.; Kim, K. S. Org. Lett. 2006, 8, 3971-3974.
54. 3NHF, less acidic than HF-pyridine but yet a good source of fluoride ion ( McClinton, M. A. Aldrichim. Acta 1995, 28, 31-35), left compound 3a unchanged.
55. Reaction at -378°C (HF-py, 20 equiv) was sluggish, leaving considerable amounts of unreacted 1,2-orthoester among other compounds, in a complex reaction mixture.
56. Neither 1,6-anhydro derivative formation or 1,2,6 internal orthoester formation were observed:Hiranuma, S.; Kanie, O.; Wong, C.-H. Tetrahedron Lett. 1999, 40, 6423-6426.
57. (a) Hall, L. D.; Steiner, P. R.; Pedersen, C. Can. J. Chem. 1970, 48, 1155-1165.
58. (b) Hall, L. D.; Manville, J. F.; Bhacca, N. S. Can. J. Chem. 1969, 47, 1-17.
59. (a) Jayaprakash, K. N.; Radhakrishnan, K. V.; Fraser-Reid, B. Tetrahedron Lett. 2002, 43, 6953-6955.
60. (b) Jayaprakash, K. N.; Fraser-Reid, B. Synlett 2004, 301-305.
61. (a) Uriel, C.; Agocs, A.; Gómez, A. M.; López, J. C.; Fraser-Reid, B. Org. Lett. 2005, 7, 4899-4902.
62. (b) López, J. C.; Gómez, A. M.; Uriel, C.; Fraser-Reid, B. Tetrahedron Lett. 2003, 44, 1417-1420.
63. A minor saccharide (3-5%) was also detected although its structure remains, at this time, uncertain.
64. Fraser-Reid, B.; Grimme, S.; Piacenza, M.; Mach, M.; Schlueter, U. Chem.-Eur. J. 2003, 9, 4687-4692.
65. Middleton, W. J. J. Org. Chem. 1975, 40, 574-578.
66. (a) Nicolaou, K. C.; Ladduwahetty, T.; Randall, J. L.; Chucholowski, A. J. Am. Chem. Soc. 1986, 108, 2466-2467.
67. (b) Nicolaou, K. C.; Rodriguez, R. M.; Mitchell, H. J.; Suzuki, H.; Fylaktakidou, K. C.; Baudoin, O.; van Delft, F. L. Chem.-Eur. J. 2000, 6, 3095-3115.
68. Lin, P.-C.; Adak, A. K.; Ueng, S.-H.; Huang, L.-D.; Huang, K.-T.; Ho, J. A.; Lin, C.-C. J. Org. Chem. 2009, 74, 4041-4048.
69. 1,2-Orthoesters are normally prepared from fully acylated derivates, thus removal of the protecting groups prior to fluoride formation have the advantage of preserving the 2-O-acyl substituent as a masked, base stable substituent.