Influence of Silyl Protections on the Anomeric Reactivity of Galactofuranosyl Thioglycosides and Application of the Silylated Thiogalactofuranosides to One-Pot Synthesis of Diverse beta-D-Oligogalactofuranosides
Influence of Silyl Protections on the Anomeric Reactivity of Galactofuranosyl Thioglycosides and Application of the Silylated Thiogalactofuranosides to One-Pot Synthesis of Diverse beta-D-Oligogalactofuranosides
复制标题
甲硅烷基保护对呋喃半乳糖苷异头反应性的影响及硅烷化硫代呋喃半乳糖苷在一锅法合成多种β-D-低聚呋喃半乳糖苷中的应用
DOI：
10.1021/jo5018684
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发表时间：
2014
影响因子：
3.6
通讯作者：
Yang Jin-Song
中科院分区：
文献类型：
--
作者：
Wang Shuai;Meng Xue;Huang Wei;Yang Jin-Song
本文研究了硅基保护基对呋喃半乳糖基苯基硫代糖苷供体反应性的调节作用。发现半乳糖呋喃糖环上的甲硅烷基醚对糖基化反应性具有武装效应，但环状3，5-缩醛保护基降低了反应性。反应性苯基2，6-二-O-Bz-3，5-二-O-TBS-1-硫代-β-d-半乳糖呋喃糖苷3被证明是一种有用的糖基结构单元。通过利用该供体，我们实现了具有不同糖苷键的β-d-呋喃半乳糖基三糖和四糖的高效一锅溶液相组装。
We describe in this paper the tuning effect of silyl protecting groups on the donor reactivity of galactofuranosyl phenyl thioglycosides. Silyl ethers on the galactofuranose ring are found to have an arming effect on the glycosylation reactivity, but the cyclic 3,5-acetal protecting group decreases the reactivity. The reactive phenyl 2,6-di-O-Bz-3,5-di-O-TBS-1-thio-β-d-galactofuranoside3is proved to be a useful glycosyl building block. By taking advantage of this donor, we achieved the highly efficient one-pot solution-phase assembly of a panel of β-d-galactofuranosyl tri- and tetrasaccharides possessing diverse glycosidic linkages.