Synthesis of oligo(α- d -glycosyl phosphate) derivatives by a phosphoramidite method via boranophosphate intermediates

Journal of Organic Chemistry

Volumn 76, Issue 8, 2011, Pages 2648-2659

  Fujita, Shoichi ^a   Oka, Natsuhisa ^a   Matsumura, Fumiko ^a   Wada, Takeshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORONATION; DEPROTECTION; DIESTERS; EFFICIENT METHOD; GLYCOSYL; HYDROXY GROUPS; LEISHMANIA; MONOMER UNITS; PHOSPHONATES; PHOSPHORAMIDITES;

CARBOHYDRATES; OLIGOMERS;

MONOMERS;

CARBOHYDRATE; IODIDE; LIPOPHOSPHOGLYCAN; OLIGO(ALPHA DEXTRO GLYCOSYL BORANOPHOSPHATE) DERIVATIVE; OLIGOMER; PHOSPHATE; PHOSPHONIC ACID DERIVATIVE; PHOSPHORAMIDOUS ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DEPROTECTION REACTION; POLYMERIZATION; SYNTHESIS;

ANTIPROTOZOAL AGENTS; BORANES; BORON; ESTERS; GLYCOCALYX; GLYCOSPHINGOLIPIDS; GLYCOSYLATION; HUMANS; LEISHMANIA; LEISHMANIASIS; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOSACCHARIDES; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHATES; PHOSPHITES; PHOSPHONIC ACIDS; POLYMERIZATION;

EID: 79953903056     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102584g     Document Type: Article

References (38)

1. Bundle, D. R.; Smith, I. C. P.; Jennings, H. J. J. Biol. Chem. 1974, 249, 2275-2281
2. Jennings, H. J.; Rosell, K.-G.; Carlo, D. J. Can. J. Chem. 1980, 58, 1069-1074
3. Hansson, J.; Oscarson, S. Curr. Org. Chem. 2000, 4, 535-564
4. Mendonça-Previato, L.; Todeschini, A. R.; Heise, N.; Agrellos, O. A.; Dias, W. B.; Previato, J. O. Curr. Org. Chem. 2008, 12, 926-939
5. Trotter., C. L.; McVernon, J.; Ramsay, M. E.; Whitney, C. G.; Mulholland, E. K.; Goldblatt, D.; Hombach, J.; Kieny, M.-P. Vaccine 2008, 26, 4434-4445
6. Joshi, V. S.; Bajaj, I. B.; Survase., S. A.; Singhal, R. S.; Kennedy, J. F. Carbohydr. Polym. 2009, 75, 553-565
7. Nikolaev, A. V.; Botvinko, I. V.; Ross, A. J. Carbohydr. Res. 2007, 342, 297-344
8. Westerduin, P.; Veeneman, G. H.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1986, 27, 6271-6274
9. Nikolaev, A. V.; Chudek, J. A.; Ferguson, M. A. J. Carbohydr. Res. 1995, 272, 179-189
10. Ross, A. J.; Ivanova, I. A.; Higson, A. P.; Nikolaev, A. V. Tetrahedron Lett. 2000, 41, 2449-2452
11. Routier, F. H.; Higson, A. P.; Ivanova, I. A.; Ross., A. J.; Tsvetkov, Y. E.; Yashunsky, D. V.; Bates, P. A.; Nikolaev, A. V.; Ferguson, M. A. J. Biochemistry 2000, 39, 8017-8025
12. Berkin, A.; Coxon, B.; Pozsgay, V. Chem. - Eur. J. 2002, 8, 4424-4433
13. Higson, A. P.; Ross., A. J.; Tsvetkov, Y. E.; Routier, F. H.; Sizova, O. V.; Ferguson, M. A. J.; Nikolaev, A. V. Chem. - Eur. J. 2005, 11, 2019-2030
14. Nikolaev, A. V.; Ivanova, I. A.; Shibaev, V. N. Carbohydr. Res. 1993, 242, 91-107
15. Hansson, J.; Garegg, P. J.; Oscarson, S. J. Org. Chem. 2001, 66, 6234-6243
16. Ruhela, D.; Vishwakarma, R. A. J. Org. Chem. 2003, 68, 4446-4456
17. Slättegaišrd, R.; Teodorovic, P.; Kinfe, H. H.; Ravenscroft, N.; Gammon, D. W.; Oscarson, S. Org. Biomol. Chem. 2005, 3, 3782-3787
18. Greimel, P.; Ito, Y. Tetrahedron Lett. 2008, 49, 3562-3566
19. Greimel, P.; Lapeyre, M.; Nagatsuka, Y.; Hirabayashi, Y.; Ito, Y. Bioorg. Med. Chem. 2008, 16, 7210-7217
20. Matsumura, F.; Oka, N.; Wada, T. Org. Lett. 2008, 10, 5297-5300
21. Matsumura, F.; Oka, N.; Wada, T. Org. Lett. 2008, 10, 1557-1560
22. Sato, K.; Oka, N.; Fujita, S.; Matsumura, F.; Wada, T. J. Org. Chem. 2010, 75, 2147-2156
23. Westerduin, P.; Veeneman, G. H.; Marugg, J. E.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1986, 27, 1211-1214
24. Kondo, H.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 8748-8750
25. Majumdar, D.; Elsayed, G. A.; Buskas, T.; Boons, G.-J. J. Org. Chem. 2005, 70, 1691-1697
26. Imamoto, T.; Nagato, E.; Wada, Y.; Masuda, H.; Yamaguchi, K.; Uchimaru, T. J. Am. Chem. Soc. 1997, 119, 9925-9926
27. Ross, A. J.; Higson, A. P.; Ferguson, M. A. J.; Nikolaev, A. V. Tetrahedron Lett. 1999, 40, 6695-6698
28. Prosperi, D.; Panza, L.; Poletti, L.; Lay, L. Tetrahedron 2000, 56, 4811-4815
29. Li, P.; Sergueeva, Z. A.; Dobrikov, M.; Shaw, B. R. Chem. Rev. 2007, 107, 4746-4796
30. Beaucage, S. L.; Iyer, R. P. Tetrahedron 1992, 48, 2223-2311
31. Watanabe, Y.; Nakamoto, C.; Yamamoto, T.; Ozaki, S. Tetrahedron 1994, 50, 6523-6536
32. Shimizu, M.; Tamura, K.; Wada, T.; Saigo, K. Tetrahedron Lett. 2004, 45, 371-374
33. Kawanaka, T.; Shimizu, M.; Wada, T. Tetrahedron Lett. 2007, 48, 1973-1976
34. Kawanaka, T.; Shimizu, M.; Shintani, N.; Wada, T. Bioorg. Med. Chem. Lett. 2008, 18, 3783-3786
35. Crich, D. Acc. Chem. Res. 2010, 8, 1144-1153
36. Mydock, L. K.; Demchenko, A. V. Org. Biomol. Chem. 2010, 8, 497-510
37. Isbell, H. S.; Frush, H. L. J. Org. Chem. 1958, 23, 1309-1319
38. See Supporting Information.