Subscribe to RSS
DOI: 10.1055/s-0033-1340620
Practical Synthesis of Building Blocks for Oligosaccharides Containing the β-d-Galp-(1→3)-β-d-GlcpNAc Motif
Publication History
Received: 29 November 2013
Accepted: 19 December 2013
Publication Date:
30 January 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201406/lookinside/thumbnails/10.1055-s-0033-1340620-1.jpg)
Abstract
An efficient, new pathway for the synthesis of the title sequence has been developed. The sequence has been obtained as a glycosyl donor, β-d-Galp-(1→3)-β-d-GlcpNAc-1-SEt, or equipped with a linker (spacer) suitable for conjugation to other molecules, β-d-Galp-(1→3)-β-d-GlcpNAc-1-(OCH2CH2)3N3. Both disaccharides have been obtained in crystalline condition for the first time and fully characterized. The existing synthesis of the intermediate disaccharide glycosyl donor was improved by conducting the silver triflate mediated glycosylation under base-deficient conditions in the presence of 1,1,3,3-tetramethylurea and in the absence of molecular sieves.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Essentials of Glycobiology . 2nd ed; Varki A, Cummings RD, Esko JD, Freeze HH, Stanley P, Bertozzi CR, Hart GW, Etzler ME. Cold Spring Harbor Laboratory Press; New York: 2008
- 2 Kunz C, Rudloff S, Baier W, Klein N, Strobel S. Annu. Rev. Nutr. 2000; 20: 699
- 3 Holgersson J, Lofling J. Glycobiology 2006; 16: 584
- 4 Bertozzi CR, Kiessling LL. Science 2001; 291: 2357
- 5 Ruttens B, Kováč P. Helv. Chim. Acta 2006; 89: 320
- 6 Ruttens B, Saksena R, Kováč P. Eur. J. Org. Chem. 2007; 4366
- 7 Sherman AA, Yudina ON, Mironov YV, Sukhova EV, Shashkov AS, Menshov VM, Nifantiev NE. Carbohydr. Res. 2001; 336: 13
- 8 Vibert A, Lopin-Bon C, Jacquinet J.-C. Tetrahedron Lett. 2010; 51: 1867
- 9 Schroeder LR, Counts KM, Haigh FC. Carbohydr. Res. 1974; 37: 368
- 10 Hou S, Kováč P. Carbohydr. Res. 2011; 346: 1394
- 11 Banoub J, Bundle DR. Can. J. Chem. 1979; 57: 2091
- 12 Garegg PJ, Norberg T. Acta Chem. Scand., Ser. B 1979; 33: 116
- 13 Freshly crystallized and thoroughly dried. Amorphous material or crystalline material that had been stored for a longer time may be partially hydrolyzed and contain a small amount of HBr. Introducing such material into the reaction mixture may, eventually, change the acidity of the reaction mixture, resulting in (partial) cleavage of the benzylidene group.