6''-修饰 α-GalCer 类似物的发散合成方法。
Divergent synthetic approach to 6''-modified α-GalCer analogues.
机构信息
Laboratory for Medicinal Chemistry (FFW), Faculty of Pharmaceutical Sciences, UGent, Harelbekestraat 72, B-9000 Gent, Belgium.
出版信息
Org Biomol Chem. 2011 Dec 21;9(24):8413-21. doi: 10.1039/c1ob06235b. Epub 2011 Nov 1.
Abstract
A synthetic approach is presented for the synthesis of galacturonic acid and D-fucosyl modified KRN7000. The approach allows for late-stage functionalisation of both the sugar 6''-OH and the sphingosine amino groups, which enables convenient synthesis of promising 6''-modified KRN7000 analogues.
摘要
本文提出了一种合成半乳糖醛酸和 D-岩藻糖基修饰 KRN7000 的方法。该方法允许在糖基 6''-OH 和神经酰胺氨基后期进行功能化，这使得有前途的 6''-修饰 KRN7000 类似物的方便合成成为可能。
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EMBO J. 2011 Jun 1;30(11):2294-305. doi: 10.1038/emboj.2011.145. Epub 2011 May 6.
2
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3
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J Am Chem Soc. 2008 Sep 17;130(37):12348-54. doi: 10.1021/ja8012787. Epub 2008 Aug 20.
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