One-pot oligosaccharide synthesis: Reactivity tuning by post-synthetic modification of aglycon

Chemical Communications

Volumn , Issue 17, 2004, Pages 1960-1961

  Huang, Lijun ^a   Wang, Zhen ^a   Huang, Xuefei ^a  

^a UNIVERSITY OF TOLEDO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AGLYCONE; CARBOHYDRATE; GLYCOSIDE; OLIGOSACCHARIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL MODIFICATION; CHEMOREACTIVITY; ONE POT SYNTHESIS; POST SYNTHETIC MODIFICATION; REACTION ANALYSIS;

EID: 5044229902     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b405886k     Document Type: Article

References (27)

1. K. M. Koeller and C.-H. Wong, Chem. Rev., 2000, 100, 4465 and pertinent references therein.
2. (a) K.-K. T. Mong and C.-H. Wong, Angew. Chem., Int. Ed., 2002, 41, 4087;
3. (b) T. K.-K. Mong, H.-K. Lee, S. G. Duron and C.-H. Wong, Proc. Natl. Acad. Sci. U. S. A., 2003, 100, 797;
4. (c) F. Burkhart, Z. Zhang, S. Wacowich-Sgarbi and C.-H. Wong, Angew. Chem., Int. Ed., 2001, 40, 1274;
5. (d) H. Tanaka, M. Adachi, H. Tsukamoto, T. Ikeda, H. Yamada and T. Takahashi, Org. Lett., 2002, 4, 4213;
6. (e) Z. Zhang, K. Niikura, X. Huang and C.-H. Wong, Can. J. Chem., 2002, 80, 1051;
7. (f) T. K. Ritter, K.-K. T. Mong, H. Liu, T. Nakatani and C.-H. Wong, Angew. Chem., Int. Ed., 2003, 42, 4657.
8. (a) L. Green, B. Hinzen, S. J. Ince, P. Langer, S. V. Ley and S. L. Warriner, Synlett, 1998, 440;
9. (b) N. L. Douglas, S. V. Ley, U. Lucking and S. L. Warriner, J. Chem. Soc., Perkin Trans. 1, 1998, 51;
10. (c) M. Fridman, D. Solomon, S. Yogev and T. Baasov, Org. Lett., 2002, 4, 281;
11. (d) S. Raghavan and D. Kahne, J. Am. Chem. Soc., 1993, 115, 1580;
12. (e) T. Takahashi, M. Adachi, A. Matsuda and T. Doi, Tetrahedron Lett., 2000, 41, 2599;
13. (f) H. Yamada, T. Harada and T. Takahashi, J. Am. Chem. Soc., 1994, 116, 7919.
14. Z. Zhang, I. R. Oilman, X.-S. Ye, R. Wischnat, T. Baasov and C.-H. Wong, J. Am. Chem. Soc., 1999, 121, 734.
15. R. J. Hinklin and L. L. Kiessling, J. Am. Chem. Soc., 2001, 123, 3379. The reactivities of these novel sulfonylcarbamate donors can be readily adjusted with various N-alkyl groups, although it remains to be shown that it is sufficient to enable one-pot synthesis.
16. S. Cao, F. Hernandez-Mateo and R. Roy, J. Carbohydr. Chem., 1998, 17, 609 and pertinent references therein. 4-Nitrophenyl thioglycosides have been used in the innovative active-latent glycosylation strategy. However, algycon adjustment on intermediates is necessary to assemble large oligosaccharides using this approach.
17. M. Lahmann and S. Oscarson, Org. Lett., 2000, 2, 3881.
18. (a) R. Geurtsen and G. J. Boons, Tetrahedron Lett., 2002, 43, 9429;
19. (b) M. Lahmann and S. Oscarson, Can. J. Chem., 2002, 80, 889.
20. T. J. Broxton, J. F. Bunnett and C. Paik, J. Org. Chem., 1977, 42, 643.
21. M. D. Andrus, S. N. Mettach and C. Song, J. Org. Chem., 2003, 67, 8284.
22. 1 as 7. Therefore, the mixture was used without further separation.
23. V. Martichonok and G. M. Whitesides, J. Org. Chem., 1996, 61, 1702.
24. There are also several minor unidentified side products in the crude reaction mixture, which could be due to addition of succinimide to the activated donor, see ref. 4.
25. (a) J. Banoub, P. Boullanger and D. Lafont, Chem. Rev., 1992, 92, 1167;
26. (b) D. Crich and V. Dudkin, J. Am. Chem, Soc., 2001, 123, 6819.
27. D. Crich and M. Smith, J. Am. Chem. Soc., 2001, 123, 9015.