Stereoselective iterative one-pot synthesis of N-glycolylneuraminic acid-containing oligosaccharides

Organic Letters

Volumn 10, Issue 18, 2008, Pages 4033-4035

  Crich, David ^a   Wu, Baolin ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

N GLYCOLOYLNEURAMINIC ACID; N-GLYCOLYLNEURAMINIC ACID; NEURAMINIC ACID DERIVATIVE; OLIGOSACCHARIDE; OXAZOLIDINONE DERIVATIVE;

ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; HUMAN; HYDROLYSIS; STEREOISOMERISM; SYNTHESIS;

HUMANS; HYDROLYSIS; NEURAMINIC ACIDS; OLIGOSACCHARIDES; OXAZOLIDINONES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 55949092054     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801548k     Document Type: Article

References (35)

1. (a) Okamoto, K.; Goto, T. Tetrahedron 1990, 46, 5835-5857.
2. (b) Hasegawa, A. In Modern Methods in Carbohydrate Synthesis; Khan, S. H., O'Niell, R. A., Eds.; Harwood Academic Publishers: Amsterdam, 1996, pp 277-300.
3. (c) Hasegawa, A.; Kiso, M. Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1997; pp 357-379.
4. (d) Kiso, M.; Ishida, H.; Ito, H. Carbohydrates in Chemistry and Biology: Chemistry of Saccharides; Ernst, B., Hart, G. W., Sinaÿ, P., Eds.; Wiley-VCH: Weinheim, 2000; Vol. 1, pp 345-365.
5. (e) Boons, G.-J.; Demchenko, A. V. Chem. Rev. 2000, 100, 4539-4565.
6. (f) Boons, G.-J.; Demchenko. A. V. Carbohydrate-Based Drug Discovery; Wong, C.-H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 1, pp 55-102.
7. (g) Ress, D. K.; Linhardt, R. J. Curr. Org. Synth. 2004, 31-46.
8. (a) Tanaka, H.; Nishiura, Y.; Adachi, M.; Takahashi, T. Heterocycles 2006, 67, 107-112.
9. (b) De Meo, C.; Priyadarshani, U. Carbohydr. Res. 2008, 343, 1540-1552.
10. (a) Hossain, N.; Magnusson, G. Tetrahedron Lett. 1999, 40, 2217-2220.
11. (b) Demchenko, A. V.; Boons, G.-J. Chem. - Eur. J. 1999, 5, 1278-1283.
12. (c) Tanaka, K; Goi, T.; Fukase, K Synlett 2005, 295, 8-2962.
13. (d) Tanaka, H.; Nishiura, Y.; Takahashi, T. J. Am. Chem. Soc. 2006, 128, 7124-7125.
14. (e) Farris, M. D.; De Meo, C Tetrahedron Lett. 2007, 48, 1225-1227.
15. (a) Huang, X.; Huang, L.; Wang, H.; Ye, X.-S. Angew. Chem., Int. Ed. 2004, 43, 5221-5224.
16. (b) Wang, Y.; Huang, X.; Zhang, L.-H.; Ye, X.-S. Org. Lett. 2004, 6, 4415-4417.
17. (c) Huang, L.; Huang, X. Chem. - Eur. J. 2007, 13, 529-540.
18. Indeed, previous strategies directed toward the one-pot synthesis of sialylated oligosaccharides have necessitated the inclusion of the sialyl moiety as part of a disaccharide, thereby circumventing the issue of the low reactivity of sialic acid thioglycosides: Zhang, Z.; Niikura, K.; Huang, X.-F.; Wong, C.-H Can. J. Chem. 2002, 80, 1051-1054.
19. Crich, D.; Li, W. J. Org. Chem. 2007, 72, 2387-2391.
20. Crich, D.; Li, W. J. Org. Chem. 2007, 72, 7794-7797.
21. (a) Blixt, O.; Paulson, J. C. Adv. Synth. Catal. 2006, 345, 687-690.
22. (b) Malykh, Y. N.; Shaw, S. R. L. Biochimie 2001, 83, 623-634.
23. (c) Varki, A. Biochimie 2001, 63, 615-622.
24. (d) Angata, T.; Varki, A. Chem. Rev. 2002, 102, 439-469.
25. C1,H3ax coupling constants: (a) Hori, H.; Nakajima, T.; Nishida, Y.; Ohrui, H.; Meguro, H. Tetrahedron Lett. 1988, 29, 6317-6320.
26. (b) Haverkamp, J.; Spoormaker, T.; Dorland, L.; Vliegenthart, J. F. G.; Schauer, R. J. Am. Chem. Soc. 1979, 101, 4851-4853.
27. (c) Prytulla, S.; Lauterwein, J.; Kiessinger, M.; Thiem, J. Carbohydr. Res. 1991, 215, 345-349.
28. (a) Spijker, N. M.; van Boeckel, C. A. A. Angew. Chem., Int. Ed. 1991, 30, 180-183.
29. (b) Jayaprakash, K. N.; Chaudhuri, S. R.; Murty, C. V. S. R.; Fraser-Reid, B. J. Org. Chem. 2007, 72, 5534-5545.
30. (c) Cid, M. B.; Alonso, I.; Alfonso, F.; Bonilla, J. B.; López-Prados, J.; Martín-Lomas, M. Eur. J. Org. Chem. 2006, 394, 7-3959.
31. The use of the phenylthio glycoside corresponding to 6 resulted in lower yields and more complex reaction mixtures. For the relative reactivities of substituted arylthio glycosides, see: Huang, L.; Wang, Z.; Huang, X. Chem. Commun. 2004, 1960-1961.
32. The use of acid washed molecular sieves gives enhanced yields in this coupling process as compared to standard 4 Å molecular sieves. This appears to be because catalytic triflic acid can be employed in the case of the acid-washed sieves, as opposed to the suprastoichiometric amounts needed with the standard sieves which ultimately results in degradation of the glycosidic bond on warming.
33. 4 that incorporation of the third sugar in the form of a hydroxyl thioglycoside would allow further chain extension.
34. This observation differs from the N-acetyl series, when it is possible to cleave the oxazolidinone selectively leaving the acetamide in place, and bears witness to the enhanced reactivity of the glycolyl carbonyl group.
35. Our inability to cleave the oxazolidinone selectively and the consequent need to resort to full saponification and subsequent reintroduction of the amide group beg the question as to the need for the acetylglycolyl group at the level of the glycosylation reaction, particularly in view of the work of Takahashi and DeMeo. In the event, however, glycosylation of donor 3 with acceptor 6 under the conditions employed in this study afforded the disaccharide 16 in 61 % yield as a 1:1 mixture of anomers. This selectivity stands in evident contrast to that of Scheme 2 and highlights the advantage of the more electron-deficient N-acyl oxazolidinone that features in our design. (Chemical Equation Presented)