Trimethylsilylnitrate-Trimethylsilyl Azide: A Novel Reagent System for the Synthesis of 2-Deoxyglycosyl Azides from Glycals. Application in the Synthesis of 2-Deoxy-β-N-glycopeptides

Journal of Organic Chemistry

Volumn 69, Issue 7, 2004, Pages 2630-2633

  Reddy, B Gopal ^a   Madhusudanan, K P ^b   Vankar, Yashwant D ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; DERIVATIVES; SUGARS; SYNTHESIS (CHEMICAL);

GLUCALS; REAGENT SYSTEMS;

AROMATIC HYDROCARBONS;

2 DEOXY BETA N GLYCOPEPTIDE; 2 DEOXYGLYCOPYRANOSYL AZIDE; AMINO ACID; AZIDE; CARBOHYDRATE; GLYCOPEPTIDE; GLYCOSIDE; REAGENT; SUGAR; TRIMETHLSILYL AZIDE; TRIMETHYLSILYLNITRATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GEOMETRY; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

AZIDES; CARBOHYDRATES; CATALYSIS; CHEMISTRY, ORGANIC; GLYCOPEPTIDES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM;

EID: 1842607477     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0354948     Document Type: Article

References (55)

1. (a) Varki, A. Glycobiology 1993, 3, 97.
2. (b) Davis, B. G. J. Chem. Soc., Perkin Trans. 1 1999, 3215.
3. (c) Arsequell, G.; Valencia, G. Tetrahedron: Asymmetry 1999, 10, 3045.
4. (a) Bertozzi, C. R.; Kiessling, L. Science 2001, 291, 2357.
5. (b) Rudd, P. M.; Elliott, T.; Creswell, P.; Wilson, I. A.; Dwek, R. A. Science 2001, 291, 2370.
6. Dwek, R. A.; Butters, T. D.; Platt, F. M.; Zitzmann, N. Nature 2002, 1, 65.
7. (a) Davis, B. G. Chem. Rev. 2002, 102, 579.
8. (b) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495.
9. (c) Dondoni, A.; Marra, A. Chem. Rev. 2000, 100, 4395.
10. (d) Peluso, S.; Imperiali, B. Tetrahedron Lett. 2001, 42, 2085.
11. (e) Dondoni, A.; Mariotti, G.; Marra, A. Tetrahedron Lett. 2000, 41, 3483.
12. (f) Nolen, E. G.; Kurish A. J.; Wong, K. A.; Orlando, M. D. Tetrahedron Lett. 2003, 44, 2449.
13. (a) Shibata, S.; Miyagawa, Y.; Naruse, T.; Takuma, T. J. Immunol. 1969, 102, 593.
14. (b) Shibata. S.; Nagasawa, T. J. Immunol. 1971, 106, 1284.
15. (a) Shibata, S.; Takeda, T.; Utsuno, A.; Okamoto, N.; Ogihara, Y. Carbohydr. Res. 1990, 207, 71.
16. (b) Sasaki, M.; Tachibana, K.; Nakanishi, H. Tetrahedron Lett. 1991, 32, 6873.
17. Laupichler, L.; Sowa, C. E.; Thiem, J. Biorg. Med. Chem. 1994, 2, 1281.
18. (a) Thiem, J.; Klaffke, W. Top. in Curr. Chem. 1990, 154, 285.
19. (b) Roush, W. R.; Hartz, R. A.; Gustin, D. J. J. Am. Chem. Soc. 1999, 121, 1990.
20. (a) Györgydeák, Z.; Szilágyi, L.; Pausen, H. J. Carbohydr. Chem. 1993, 12, 139.
21. (b) Györgydeák, Z.; Thiem, J. Carbohydr. Res. 1995, 268, 85.
22. Štimac, A.; Kobe, J. Carbohydr. Res. 2000, 329, 317.
23. Ying, L.; Gervay-Hague, J. Carbohydr. Res. 2003, 338, 835.
24. (a) Kirschning, A.; Hashem, M. A.; Monenschein, H.; Rose, L.; Schöning, K.-U. J. Org. Chem. 1999, 64, 6522.
25. (b) Kirschning, A.; Jesberger, M.; Monenschein, H. Tetrahedron Lett. 1999, 40, 8999.
26. (a) Kawabata, H.; Kubo, S.; Hayashi, M. Carbohydr. Res. 2001, 333, 153.
27. (b) Yadav, J. S.; Reddy, B. V. S.; Chand, P. K. Tetrahedron Lett. 2001, 42, 4057.
28. (c) Yadav, J. S.; Reddy, B. V. S. Synthesis 2002, 511.
29. (a) Rani, S.; Vankar, Y. D. Tetrahedron Lett. 2003, 44, 907.
30. (b) Pachamuthu, K.; Das, J.; Gupta, A.; Schmidt, R. R.; Vankar, Y. D. Eur. J. Org. Chem. 2002, 1479.
31. (c) Reddy, B. G.; Vankar, Y. D. Tetrahedron Lett. 2003, 44, 4765.
32. (d) Pachamuthu, K.; Vankar, Y. D. J. Org. Chem. 2001, 66, 7511.
33. (e) Gupta, A.; Vankar, Y. D. Tetrahedron 2000, 56, 8525.
34. (f) Rani, S.; Agarwal, A.; Vankar, Y. D. Tetrahedron Lett. 2003, 44, 5001.
35. (a) Shahi, S. P.; Gupta, A.; Pitre, S. V.; Reddy, M. V. R.; Kumareswaran, R and Vankar, Y. D. J. Org. Chem. 1999, 64, 4509.
36. (b) Reddy, M. V. R.; Kumareswaran, R.; Vankar, Y. D. Tetrahedron Lett. 1995, 36, 7149.
37. Kimura, M.; Kajita, K.; Onoda, N.; Morosawa, S. J. Org. Chem. 1990, 55, 4887.
38. 4 conformation. Likewise, the configuration at H-1 in 4d and its structure was established.
39. (a) Ollivier, C.; Renaud, P. J. Am. Chem. Soc. 2001, 123, 4717.
40. (b) Huang, X.; Surry, C.; Hiebert, T.; Bennet, A. J. J. Am. Chem. Soc. 1995, 117, 10614.
41. (c) Szarek, W.; Achmatowicz, Jr. O.; Plenkiewicz, J.; Radatus, B. K. Tetrahedron 1978, 34, 1427.
42. Lemieux, R. U.; Ratcliffe, R. M. Can. J. Chem. 1979, 57, 1244.
43. The pH of the reaction mixture was found to be 2.5.
44. (a) Boullanger, P.; Maunier, V.; Lafont, D. Carbohydr. Res. 2000, 324, 97.
45. (b) Kovács, L.; Ösz, E.; Domokos, V.; Holzer, W.; Györgydeák, Z. Tetrahedron 2001, 57, 4609.
46. (c) Sridhar, P. R.; Prabhu, K. R.; Chandarsekaran, S. J. Org. Chem. 2003, 68, 5261 and references therein.
47. Damkaci, F.; DeShong, P. J. Am. Chem. Soc. 2003, 125, 4408.
48. Suga, H.; Ersoy, O.; Tsumuraya, T.; Lee, J.; Sinskey, A. J. J. Am. Chem. Soc. 1994, 116, 487.
49. Suzuki, T.; Suzuki, S. T.; Yamada, I.; Koashi Y.; Yamada, K.; Chida, N. J. Org. Chem. 2002, 67, 2874 and references therein.
50. Cohen-Anisfeld, S. T.; Lansbury, P. T. J. Am. Chem. Soc. 1993, 115, 10531.
51. For other syntheses of 2-deoxy-N-glycoppetides, see: (a) Isac-Garcia, J. ; Carvo-Flores, F. G.; Hernandez-Mateo, F.; Santoyo-Gonzalez, F. Eur. J. Org. Chem. 2001, 383.
52. (b) Urge, L.; Otvos, Jr. L.; Lang, E.; Wroblewski, K.; Laczko, I.; Hollosi, M. Carbohydr. Res. 1992, 235, 83.
53. (a) Gruner, S. A. W.; Locardi, E.; Lohof, E.; Kessler, H. Chem. Rev. 2002, 102, 491.
54. (b) Schweizer, F. Angew. Chem. 2002, 114, 240. Angew. Chem., Int. Ed. 2002, 41, 230.
55. (b) Schweizer, F. Angew. Chem. 2002, 114, 240. Angew. Chem., Int. Ed. 2002, 41, 230.