Superarming of Glycosyl Donors by Combined Neighboring and Conformational Effects
作者： Mads Heuckendorff , Hemali D. Premathilake , Papapida Pornsuriyasak , Anders Ø. Madsen , Christian M. Pedersen
DOI: 10.1021/OL402371B
关键词:
摘要: A novel glycosyl donor that combines the concepts of both conformational and electronic superarming has been synthesized. The reactivity selectivity have tested in competition experiments.
acs.org
core.ac.uk 
sci-hub.se 参考文章(44)
Hemali D. Premathilake, Alexei V. Demchenko, Superarmed and superdisarmed building blocks in expeditious oligosaccharide synthesis. Topics in Current Chemistry. ,vol. 301, pp. 189- 221 ,(2010) , 10.1007/128_2010_106
Bruce G. Wilson, Bert Fraser-Reid, n-Pentenyl Glycoside Based Methodology for Determining the Relative Reactivities of Variously Protected Pairs of Glycosides Journal of Organic Chemistry. ,vol. 60, pp. 317- 320 ,(1995) , 10.1021/JO00107A008
Ciaran McDonnell, Oscar López, Paul Murphy, José G. Fernández Bolaños, Rita Hazell, Mikael Bols, Conformational Effects on Glycoside Reactivity: Study of the High Reactive Conformer of Glucose Journal of the American Chemical Society. ,vol. 126, pp. 12374- 12385 ,(2004) , 10.1021/JA047476T
Bert Fraser-Reid, Zufan Wu, Uko E. Udodong, Hakan Ottosson, Armed/disarmed effects in glycosyl donors: rationalization and sidetracking Journal of Organic Chemistry. ,vol. 55, pp. 6068- 6070 ,(1990) , 10.1021/JO00312A004
Mads Heuckendorff, Christian Marcus Pedersen, Mikael Bols, Conformationally armed 3,6-tethered glycosyl donors: synthesis, conformation, reactivity, and selectivity. Journal of Organic Chemistry. ,vol. 78, pp. 7234- 7248 ,(2013) , 10.1021/JO4012464
Yun Hsu, Xin-An Lu, Medel Manuel L. Zulueta, Chih-Ming Tsai, Kuo-I Lin, Shang-Cheng Hung, Chi-Huey Wong, Acyl and Silyl Group Effects in Reactivity-Based One-Pot Glycosylation: Synthesis of Embryonic Stem Cell Surface Carbohydrates Lc4 and IV2Fuc-Lc4 Journal of the American Chemical Society. ,vol. 134, pp. 4549- 4552 ,(2012) , 10.1021/JA300284X
Laurel K. Mydock, Alexei V. Demchenko, Superarming theS-Benzoxazolyl Glycosyl Donors by Simple 2-O-Benzoyl-3,4,6-tri-O-benzyl Protection Organic Letters. ,vol. 10, pp. 2103- 2106 ,(2008) , 10.1021/OL800345J
Nina L. Douglas, Steven V. Ley, Ulrich Lücking, Stuart L. Warriner, Tuning glycoside reactivity: New tool for efficient oligosaccharide synthesis Journal of The Chemical Society-perkin Transactions 1. pp. 51- 66 ,(1998) , 10.1039/A705275H
Bert Fraser-Reid, Zufan Wu, C. Webster Andrews, Evan Skowronski, J. Phillip Bowen, Torsional effects in glycoside reactivity: saccharide couplings mediated by acetal protecting groups Journal of the American Chemical Society. ,vol. 113, pp. 1434- 1435 ,(1991) , 10.1021/JA00004A066
Hemali D. Premathilake, Laurel K. Mydock, Alexei V. Demchenko, Superarming Common Glycosyl Donors by Simple 2-O-Benzoyl-3,4,6-tri-O-benzyl Protection Journal of Organic Chemistry. ,vol. 75, pp. 1095- 1100 ,(2010) , 10.1021/JO9021474