Lewis(x) 及二聚体Lewis(x) 的合成：通过预活化与基于反应性的化学选择性一锅法糖基化反应相结合构建支链寡糖。
Syntheses of Lewis(x) and dimeric Lewis(x): construction of branched oligosaccharides by a combination of preactivation and reactivity based chemoselective one-pot glycosylations.
作者信息
Miermont Adeline, Zeng Youlin, Jing Yuqing, Ye Xin-shan, Huang Xuefei
机构信息
Department of Chemistry, The University of Toledo, Toledo, OH 43606, USA.
出版信息
J Org Chem. 2007 Nov 9;72(23):8958-61. doi: 10.1021/jo701694k. Epub 2007 Oct 16.
Abstract
Two asymmetrically branched oligosaccharides, LewisX and dimeric LewisX, were assembled in one pot with high yields and exclusive regio- and stereoselectivities. p-Tolyl thioglycosides were utilized as the sole type of building blocks, thus simplifying the overall synthetic design. The reactivity-independent nature of the preactivation based method allows modular assembly of the dimeric LewisX octasaccharide without the need for tedious protective group manipulation to achieve exact anomeric reactivities.
摘要
两种不对称分支的寡糖，即LewisX和二聚体LewisX，在一锅反应中以高产率和专一的区域及立体选择性组装而成。对甲苯基硫代糖苷被用作唯一类型的构建单元，从而简化了整体合成设计。基于预活化方法的与反应性无关的特性允许二聚体LewisX八糖进行模块化组装，而无需繁琐的保护基操作来实现精确的端基异构反应性。
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2
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Nat Med. 2007 Mar;13(3):367-71. doi: 10.1038/nm1541. Epub 2007 Mar 4.
3
Highly efficient syntheses of hyaluronic acid oligosaccharides.
Chemistry. 2007;13(2):529-40. doi: 10.1002/chem.200601090.
4
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Chemistry. 2006 Jul 5;12(20):5246-52. doi: 10.1002/chem.200600290.
5
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Carbohydr Res. 2006 Jul 24;341(10):1669-79. doi: 10.1016/j.carres.2006.01.007. Epub 2006 Jan 26.
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Glycoconj J. 2004;21(5):251-6. doi: 10.1023/B:GLYC.0000045097.19353.73.
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Iterative one-pot synthesis of oligosaccharides.
Angew Chem Int Ed Engl. 2004 Oct 4;43(39):5221-4. doi: 10.1002/anie.200460176.
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Org Biomol Chem. 2004 Apr 21;2(8):1199-212. doi: 10.1039/b400029c. Epub 2004 Mar 15.
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