Glycosylthiomethyl Chloride: A New Species for S-Neoglycoconjugate Synthesis. Synthesis of 1-N-Glycosylthiomethyl-1,2,3-triazoles

Journal of Organic Chemistry

Volumn 69, Issue 4, 2004, Pages 1081-1085

  Zhu, Xiangming ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; CHLORIDE MINERALS; NITROGEN COMPOUNDS; SUBSTITUTION REACTIONS;

RING SUBSTITUTION;

SYNTHESIS (CHEMICAL);

1 GLYCOSYLTHIOMETHYL 1,2,3 TRIAZOLE DERIVATIVE; ACETYLENE DERIVATIVE; AMPHOLYTE; CYCLOPENTADIENE DERIVATIVE; DICHLOROMETHANE; GLYCOSYLTHIOMETHYL CHLORIDE; METHYL CHLORIDE; SODIUM AZIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; CYCLOADDITION; DIELS ALDER REACTION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

GLYCOSIDES; MOLECULAR STRUCTURE; TRIAZOLES;

EID: 1242352499     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035300o     Document Type: Article

References (77)

1. (a) Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1998.
2. (b) Meldal, M. In Neoglycoconjugates: Preparation and Applications; Lee, Y. C., Lee, R. T., Eds.; Academic Press: San Diego, 1994; p 145.
3. (c) Sears, P.; Wong, C. H. Angew. Chem., Int. Ed. 1999, 38, 2300-2324.
4. (a) Jahn, M.; Marles, J.; Warren, R. A. J.; Withers, S. G. Angew. Chem., Int. Ed. 2003, 42, 352-354.
5. (b) Witczak, Z. J.; Chhabra, R.; Chen, H.; Xie, X. Carbohydr. Res. 1997, 301, 167-175.
6. (c) Driguez, H. ChemBioChem 2001, 2, 311-318.
7. (d) Kiefel, M. J.; Thomson, R. J.; Radovanovic, M.; Itzstein, M. V. J. Carbohydr. Chem. 1999, 18, 937-959.
8. (e) Falconer, R. A. Tetrahedron Lett. 2002, 43, 8503-8505.
9. For some examples of the synthesis of S-glycoconjugates, see: (a) Eisele, T.; Schmidt, R. R. Liebigs Ann./Recueil 1997, 865-872.
10. (b) Zhu, X.; Pachamuthu, K.; Schmidt, R. R. J. Org. Chem. 2003, 68, 5641-5651.
11. (c) Zhu, X.; Schmidt, R. R. Tetrahedron Lett. 2003, 44, 6063-6067.
12. (d) Hasegawa, A.; Morita, M.; Kojima, Y.; Ishida, H.; Kiso, M. Carbohydr. Res. 1991, 214, 43-53.
13. (e) Peerlings, H. W. I.; Nepogodiev, S. A.; Stoddart, J. F.; Meijer, E. W. Eur. J. Org. Chem. 1998, 1879-1886.
14. (f) Knapp, S.; Myers, D. S. J. Org. Chem. 2001, 66, 3636-3638.
15. (g) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995-2999.
16. There are a large number of reports on the synthesis of neoglycoconjugates, particularly neoglycopeptides. For some recent examples, see: (a) Pérez-Balderas, F.; Ortega-Muñoz, M.; Morales-Sanfrutos, J.; Hernández-Mateo, F.; Calvo-Flores, F. G.; Calvo-Asín, J. A.; Isac-García, J.; Santoyo-González, F. Org. Lett. 2003, 5, 1951-1954.
17. (b) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085-2087.
18. (c) Böttcher, C.; Burger, K. Tetrahedron Lett. 2003, 44, 4223-4226.
19. (d) Pratt, M. R.; Bertozzi, C. R. J. Am. Chem. Soc. 2003, 125, 6149-6159.
20. (e) McGarvey, G. J.; Benedum, T. E.; Schmidtmann, F. W. Org. Lett. 2002, 4, 3591-3594.
21. (f) Macmillan: D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Org. Lett. 2002, 4, 1467-1470 and references therein.
22. (g) Carrasco, M. R.; Nguyen, M. J.; Burneil, D. R.; MacLaren, M. D.; Hengel, S. M. Tetrahedron Lett. 2002, 43, 5727-5729.
23. (h) Rodriguez, E. C.; Marcaurelle, L. A.; Bertozzi, C. R. J. Org. Chem. 1998, 63, 7134-7135.
24. (i) Carrasco, M. R.; Brown, R. T.; Serafimova, I. M.; Silva, O. J. Org. Chem. 2003, 68, 195-197.
25. (j) George, S. K.; Schwientek, T.; Holm, B.; Reis, C. A.; Clausen, H.; Kihlberg, J. J. Am. Chem. Soc. 2001, 123, 11117-11125.
26. (k) Marcaurelle, L. A.; Pratt, M. R.; Bertozzi, C. R. ChemBioChem 2003, 2/3, 224-228.
27. (l) Renaudet, O.; Dump, P. Org. Lett. 2003, 5, 243-246.
28. (m) Liu, H.; Wang, L.; Brock, A.; Wong, C.-H.; Schultz, P. G. J. Am. Chem. Soc. 2003, 125, 1702-1703.
29. Davis, N. I.; Flitsch, S. L. Tetrahedron Lett. 1991, 32, 6793-6796.
30. Bengtsson, M.; Broddefalk, J.; Dahmén, J.; Henriksson, K.; Kihlberg, J.; Lönn, H.; Srinivasa, B. R.; Stenvall, K. Glycoconjugate J. 1998, 15, 223-231.
31. 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984.
32. Katritzky, A. R.; Rees, C. W. In Comprehensive Heterocyclic Chemistry; Potts, K. T., Ed.; Pergamon Press: Oxford, 1984; Vol. 5, Part 4A.
33. For a review, see: Böhm, R.; Karow, C. Pharmazie 1981, 36, 243-247.
34. de las Heras, F. G.; Alonso, R.; Alonso, G. J. Med. Chem. 1979, 22, 496-501.
35. Tullis, J. S.; Van Rens, J. C.; Natchus, M. G.; Clark, M. P.; De, B.; Hsieh, L. C.; Janusz, M. J. Bioorg. Med. Chem. Lett. 2003, 18, 1665-1668.
36. Krentzberger, A.; Stratmann, J. J. Heterocycl. Chem. 1980, 17, 1505-1508.
37. Vicentini, C. B.; Manfredini, S.; Manfrini, M.; Bazzanini, R.; Musiu, C. ; Putzolu, M.; Perra, G.; Marongiu, M. E. Arch. Pharm. Pharm. Med. Chem. 1998, 331, 269-272.
38. Hartzel, L. W.; Benson, F. R. J. Am. Chem. Soc. 1954, 76, 667-670.
39. For some recent examples of the synthesis of 1,2,3-triazole derivatives without sugar substituents by 1,3-dipolar cycloadditions, see: (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
40. (b) Guerin, D. J.; Miller, S. J. J. Am. Chem. Soc. 2002, 124, 2134-2136.
41. (c) Melai, V.; Brillante, A.; Zanirato, P. J. Chem. Soc., Perkin Trans. 2 1998, 2447-2449.
42. (d) Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435-438.
43. (e) Gardiner, M.; Grigg, R.; Kordes, M.; Sridharan, V.; Vicker, N. Tetrahedron 2001, 57, 7729-7735.
44. (f) Tuncel, D.; Steinke, J. H. G. Chem. Commun. 2002, 496-497.
45. (g) Hlasta, D. J.; Ackerman, J. H. J. Org. Chem. 1994, 59, 6184-6189.
46. (h) Howell, S. J.; Spencer, N.; Philp, D. Tetrahedron 2001, 57, 4945-4954.
47. For some recent examples of the synthesis of sugar-derived 1,2, 3-triazole derivatives, see: (a) Hager, C.; Miethchen, R.; Reinke, H. J. Prakt. Chem. 2000, 342, 414-420.
48. (b) Marco-Contelles, J.; Jiménez, C. A. Tetrahedron 1999, 55, 10511-10526.
49. (c) Somsák, L.; Sós, E.; Györgydeák, Z.; Praly, J. P.; Descotes, G. Tetrahedron 1996, 52, 9121-9136.
50. (d) Šimac, A.; Leban, I.; Kobe, J. Synlett 1999, 7, 1069-1073.
51. (e) Al-Masoudi, N. A.; Al-Soud, Y. A. Tetrahedron Lett. 2002, 48, 4021-4022.
52. (f) Al-Masoudi, N. A.; Al-Soud, Y. A. Nucleosides, Nucleotides Nucleic Acids 2002, 21, 361-375.
53. (g) Chen, X. M.; Li, Z. J.; Ren, Z. X.; Huang, Z. T. Carbohydr. Res. 1999, 315, 262-267.
54. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
55. Fazio, F.; Bryan, M. C.; Blixt, O.; Paulson, J. C.; Wong, C. H. J. Am. Chem. Soc. 2002, 124, 14397-14402.
56. Wang, Q.; Chan, T. R.; Hilgraf, R.; Fokin, V. V.; Sharpless, K. B.; Finn, M. G. J. Am. Chem. Soc. 2003, 125, 3192-3193.
57. Imino-2-methoxyethyl 1-thioglycosides have been prepared and employed for attaching sugars to proteins, see: Lee, Y. C.; Stowell, C. P.; Krantz, M. J. Biochemistry 1976, 15, 3956-3963.
58. It is important to note that the new sugar species reported here has been also employed successfully in the synthesis of other S-neoglycoconjugates: Zhu, X. Unpublished results.
59. Very recently, dichloromethane has been observed to react with carbon nucleophiles, affording methylene-linked symmetric dimers, see: Armstrong, A.; Scutt, J. N. Org. Lett. 2003, 5, 2331-2334.
60. (a) Fulton, D. A.; Stoddart, J. F. J. Org. Chem. 2001, 66, 8309-8319.
61. (b) Haque, M. B.; Roberts, B. P.; Tocher, D. A. J. Chem. Soc., Perkin Trans. 1 1998, 2881-2889.
62. (c) Paul, B.; Korytnyk, W. Carbohydr. Res. 1984, 126, 27-43.
63. (d) Fujihira, T.; Chida, M.; Kamijo, H.; Takido, T.; Seno, M. J. Carbohydr. Chem. 2002, 21, 287-292.
64. (e) Staněk, J.; Šindlerová, M.; Černý, M. Collect. Czech. Chem. Commun. 1965, 30, 297-303.
65. (f) Pastuch, G.; Szeja, W. Pol. J. Chem. 2000, 74, 227-230.
66. (g) Cai, Y.; Roberts, B. P.; Tocher, D. A. J. Chem. Soc., Perkin Trans. 1 2002, 1376-1386.
67. In the course of the studies to optimize the yield of the glycosylthiomethyl chlorides, it was noted that consistently high yields could be obtained with 0.05 M thiol in dichloromethane. See Experimental Section for details.
68. Unlike entries 1-7, TLC indicated that almost no methylene-linked dimer was produced in entry 8.
69. For one more recent example, see: Löber, S.; Rodriguez-Loaiza, P.; Gmeiner, P. Org. Lett. 2003, 5, 1753-1755.
70. Deng, W. P.; Nam, G.; Fan, J.; Kirk, K. L. J. Org. Chem. 2003, 68, 2798-2802.
71. The NMR spectra of various substituted 1,2,3-triazoles have been studied and the 5-H signals of 1-substituted-1,2,3-triazoles were found to occur at lower field than the 4-H resonance; see: Elguero, J.; González, E.; Jacquier, R. Bull. Soc. Chim. Fr. 1967, 2998-3003.
72. Lehmkuhl, F. A.; Witkowski, J. T.; Robins, R. K. J. Heterocycl. Chem. 1972, 9, 1195-1201.
73. Palacios, F.; de Retana, A. M. O.; Pagalday, J. Heterocycles 1995, 40, 543-550.
74. Machin, P. J.; Hurst, D. N.; Bradshaw, R. M.; Blaber, L. C.; Burden, D. T.; Melarange, R. A. J. Med. Chem. 1984, 27, 503-509.
75. Compounds bearing a methylene group linked to both a heteroatom and a heterocyclic nitrogen atom have been investigated as potential anticancer agents, see: Garcia-Muñoz, G.; Madroñero, R.; Rico, M.; Saldaña, M. C. J. Heterocycl. Chem. 1969, 6, 921-925. On the other hand, the presence of an aromatic heterocyclic group next to the glycosidic bond may enhance the interaction between neoglycoconjugates with lectins by increasing the hydrophobicity, see ref 7 cited in ref 4a.
76. Biological studies are under way.
77. The chemical shift of 5-H proton in 33 is at a lower field than the 4-H proton in 34, which is consistent with a previous report, see: Alonso, G.; García-Lòpez, M. T.; García-Muñoz, G.; Madroñero, R.; Rico, M. J. Heterocycl. Chem. 1970, 7, 1269-1272.