The intriguing dual-directing effect of 2-cyanobenzyl ether for a highly stereospecific glycosylation reaction

作者: Kim Le Mai Hoang , Xue-Wei Liu

DOI: 10.1038/NCOMMS6051

关键词:

摘要: Glycosylation reactions can be hampered by a lack of selectivity, giving mixtures α- and β-products. Here, the authors demonstrate use 2-cyanobenzyl functionalization as directing group to give or β-selectivity from single starting material.

参考文章(49)
Akihiro Ishiwata, Yuichi Munemura, Yukishige Ito, Synergistic solvent effect in 1,2-cis-glycoside formation Tetrahedron. ,vol. 64, pp. 92- 102 ,(2008) , 10.1016/J.TET.2007.10.087
Hiroko Satoh, Halvor S. Hansen, Shino Manabe, Wilfred F. van Gunsteren, Philippe H. Hünenberger, Theoretical Investigation of Solvent Effects on Glycosylation Reactions: Stereoselectivity Controlled by Preferential Conformations of the Intermediate Oxacarbenium-Counterion Complex Journal of Chemical Theory and Computation. ,vol. 6, pp. 1783- 1797 ,(2010) , 10.1021/CT1001347
Zhiyuan Zhang, Ian R. Ollmann, Xin-Shan Ye, Ralf Wischnat, Timor Baasov, Chi-Huey Wong, Programmable one-pot oligosaccharide synthesis Journal of the American Chemical Society. ,vol. 121, pp. 734- 753 ,(1999) , 10.1021/JA982232S
Sabine Arndt, Linda C. Hsieh-Wilson, Use of cerny epoxides for the accelerated synthesis of glycosaminoglycans. Organic Letters. ,vol. 5, pp. 4179- 4182 ,(2003) , 10.1021/OL035606H
Ian Cumpstey, Intramolecular aglycon delivery Carbohydrate Research. ,vol. 343, pp. 1553- 1573 ,(2008) , 10.1016/J.CARRES.2008.04.031
Susanne A. Stalford, Colin A. Kilner, Andrew G. Leach, W. Bruce Turnbull, Neighbouring group participation vs. addition to oxacarbenium ions: studies on the synthesis of mycobacterial oligosaccharides. Organic and Biomolecular Chemistry. ,vol. 7, pp. 4842- 4852 ,(2009) , 10.1039/B914417J