S-Benzimidazolyl glycosides as a platform for oligosaccharide synthesis by an active-latent strategy.
作者信息
Hasty Scott J, Kleine Matthew A, Demchenko Alexei V
机构信息
Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, MO 63121, USA.
出版信息
Angew Chem Int Ed Engl. 2011 Apr 26;50(18):4197-201. doi: 10.1002/anie.201007212. Epub 2011 Mar 23.
Abstract
摘要
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2
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3
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Nat Chem. 2009 Nov;1(8):611-22. doi: 10.1038/nchem.399.
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J Org Chem. 2010 Feb 19;75(4):1095-100. doi: 10.1021/jo9021474.
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J Org Chem. 2009 Dec 4;74(23):9233-6. doi: 10.1021/jo901837z.
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