Divergent Synthesis of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo) Glycosides Containing alpha-(2 -> 4)-Linked Kdo-Kdo Unit
Divergent Synthesis of 3-Deoxy-d-manno-oct-2-ulosonic Acid (Kdo) Glycosides Containing alpha-(2 -> 4)-Linked Kdo-Kdo Unit
复制标题
含有 α-(2 -> 4)-连接 Kdo-Kdo 单元的 3-脱氧-d-甘露-辛-2-酮糖酸 (Kdo) 糖苷的发散合成
DOI：
10.1002/asia.201801779
复制
发表时间：
2019
影响因子：
4.1
通讯作者：
Yang Jin-Song
中科院分区：
文献类型：
--
作者：
Zhou Xian-Yang;Yang Pan;Luo Sheng;Yang Jin-Song
开发了一种方便和多样化的方法来制备含有Kdo-α-（2→4）-Kdo片段的不同细菌3-脱氧-d-甘露-辛-2-酮糖酸（Kdo）寡糖。作为共同前体的正交保护的α-（2→4）连接的Kdo-Kdo二糖苷3分别被发散地转化为相应的8-、8′-和4′-羟基二糖苷5、7和14。然后，这些醇分别用5，7-O-二叔丁基亚硅基（DTBS）保护的Kdo硫代糖苷供体1或2以α-立体选择性和高产率的方式进行糖基化，以提供一系列Kdo寡糖。最后，去除新形成的糖苷的所有保护基团产生所需的游离Kdo寡聚物。
A convenient and divergent approach was developed to prepare diverse bacterial 3‐deoxy‐d‐manno‐oct‐2‐ulosonic acid (Kdo) oligosaccharides containing a Kdo‐α‐(2→4)‐Kdo fragment. The orthogonal protected α‐(2→4) linked Kdo‐Kdo disaccharide3, serving as a common precursor, was divergently transformed into the corresponding 8‐, 8′‐, and 4′‐hydroxy disaccharides5,7, and14, respectively. Then, these alcohols were glycosylated, respectively, with the 5,7‐O‐di‐tert‐butylsilylene (DTBS) protected Kdo thioglycoside donors1or2in an α‐stereoselective and high‐yielding manner to afford a range of Kdo oligosaccharides. Finally, removal of all protecting groups of the newly formed glycosides resulted in the desired free Kdo oligomer.