Stereoselective synthesis of P-modified α-glycosyl phosphates by the oxazaphospholidine approach

Organic Letters

Volumn 15, Issue 23, 2013, Pages 5948-5951

  Noro, Mihoko ^a   Fujita, Shoichi ^a   Wada, Takeshi ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BORON DERIVATIVE; GLYCOSIDE; ORGANOPHOSPHATE; POLYSACCHARIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GLYCOCALYX; LEISHMANIA; STEREOISOMERISM; SYNTHESIS;

BORON COMPOUNDS; GLYCOCALYX; GLYCOSIDES; LEISHMANIA; MOLECULAR STRUCTURE; ORGANOPHOSPHATES; POLYSACCHARIDES; STEREOISOMERISM;

EID: 84890092051     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402785h     Document Type: Article

References (21)

1. 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
2. Joshi, V. S.; Bajaj, I. B.; Survase, S. A.; Singhal, R. S.; Kennedy, J. F. Carbohydr. Polym. 2009, 75, 553-565
3. Mendonça-Previato, L.; Todeschini, A. R.; Heise, N.; Agrellos, O. A.; Dias, W. B.; Previato, J. O. Curr. Org. Chem. 2008, 12, 926-939
4. Mendonça-Previato, L.; Todeschini, A. R.; Heise, N.; Previato, J. O. Curr. Org. Struct. Biol. 2005, 15, 499-505
5. Hansson, J.; Oscarson, S. Curr. Org. Chem. 2000, 4, 535-564
6. Nikolaev, A. V.; Botvinko, I. V.; Ross, A. J. Carbohydr. Res. 2007, 342, 297-344
7. Routier, F. H.; Higson, A. P.; Ivanova, I. A.; Ross, A. J.; Tsvetkov, Y. E.; Yashunsky, D. V.; Bates, P. A.; Nikilaev, A. V.; Ferguson, M. A. J. Biochemistry 2000, 39, 8017-8025
8. Singh, A. H.; Newborn, J. S.; Raushel, F. M. Bioorg. Chem. 1988, 16, 206-214
9. Cohen, S. B.; Halcomb, R. L. J. Org. Chem. 2000, 65, 6145-6152
10. Klinger, M. M.; McCarthy, D. J. Bioorg. Med. Chem. Lett. 1992, 2, 197-200
11. Sheu, F. R.; Frey, P. A. J. Biol. Chem. 1978, 253, 3378-3380
12. Yamazaki, Y.; Nagatsuka, Y.; Oshima, E.; Suzuki, Y.; Hirabayashi, Y.; Hashikawa, T. J. Immunol. Methods 2006, 311, 106
13. Prosperi, D.; Panza, L.; Poletti, L.; Lay, L. Tetrahedron 2000, 56, 4811-4815
14. Matsumura, F.; Oka, N.; Wada, T. Org. Lett. 2008, 8, 1557-1560
15. Oka, N.; Yamamoto, M.; Sato, T.; Wada, T. J. Am. Chem. Soc. 2008, 130, 16031-16037
16. Oka, N.; Kondo, T.; Fujiwara, S.; Maizuru, Y.; Wada, T. Org. Lett. 2009, 11, 967-970
17. Wada, T.; Maizuru, Y.; Shimizu, M.; Oka, N.; Saigo, K. Bioorg. Mol. Chem. Lett. 2006, 16, 3111-3114
18. Oka, N.; Wada, T.; Saigo, K. J. Am. Chem. Soc. 2002, 124, 4962-4967
19. Oka, N.; Wada, T.; Saigo, K. J. Am. Chem. Soc. 2003, 125, 8307-8317
20. Song, Q.; Wang, Z.; Sanghvi, Y. S. Nucleosides, Nucleotides, Nucleic Acids 2003, 22, 629-633
21. Roy, S. K.; Tang, J. Y. U.S. Patent 6, 500, 944, 2002.