Metal-Free Synthesis of Acyl Glycosides and Application to Oligosaccharide Synthesis
Metal-Free Synthesis of Acyl Glycosides and Application to Oligosaccharide Synthesis
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酰基糖苷的无金属合成及其在低聚糖合成中的应用
DOI：
10.1021/acs.orglett.2c03661
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发表时间：
2022
期刊：
影响因子：
5.2
通讯作者：
Kita Yasuyuki
中科院分区：
文献类型：
--
作者：
Morimoto Koji;Yanase Kana;Kajimoto Tetsuya;Kita Yasuyuki
低聚糖参与了许多生物过程。实现最佳的端粒选择性和区域选择性仍然具有挑战性。本文提出了一种用羧酸衍生的高价碘试剂氧化糖基化硫代糖苷形成C-O键的方法。巯基糖苷与各种高价碘羧酸盐反应得到酰基糖基化合物。这些酰基糖基化合物可与巯基糖苷受体反应生成双糖；重复此方法可合成三糖和四糖。
Oligosaccharides are involved in numerous biological processes. Achieving optimal anomeric selectivity and regioselectivity remains challenging. Herein, we present a method for the oxidative glycosylation of thioglycosides with hypervalent iodine reagents derived from carboxylic acid to form C–O bonds. The reaction of thioglycosides with various hypervalent iodine carboxylates afforded acylO-glycosyl compounds. These acylO-glycosyl compounds could react with thioglycoside acceptors to produce disaccharides; trisaccharides and tetrasaccharides could be synthesized by repeating this method.