β-Arabinofuranosylation Using 5-O-(2-Quinolinecarbonyl) Substituted Ethyl Thioglycoside Donors
β-Arabinofuranosylation Using 5-O-(2-Quinolinecarbonyl) Substituted Ethyl Thioglycoside Donors
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DOI：
10.1021/ol401755e
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发表时间：
2013-08-02
期刊：
影响因子：
5.2
通讯作者：
Yang, Jin-Song
中科院分区：
文献类型：
--
作者：
Liu, Qiang-Wei;Bin, Hua-Chao;Yang, Jin-Song
以5-O-(2-喹啉甲酰基)取代的阿拉伯糖乙基硫代糖苷为糖基供体，建立了一种新的β-立体选择性D-和L-阿拉伯呋喃糖基化方法。该方法允许使用广泛的受体底物；β选择性是从好到极好的。然后，从分枝杆菌细胞壁多糖中立体选择性地合成了甘露糖封端的八糖部分，以证明该方法的实用性。
A new beta-stereoselective D- and L-arabinofuranosylation method has been developed employing 5-O-(2-quinolinecarbonyl) substituted arabinosyl ethyl thioglycosides as glycosyl donors. The approach allows a wide range of acceptor substrates to be used; the beta-selectivity is good-to-excellent. Stereoselective synthesis of a mannose-capped octasaccharide portion from a mycobacterial cell wall polysaccharide was then carried out to demonstrate the utility of this methodology.