p-tert-Butyl Groups Improve the Utility of Aromatic Protecting Groups in Carbohydrate Synthesis
p-tert-Butyl Groups Improve the Utility of Aromatic Protecting Groups in Carbohydrate Synthesis
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DOI：
10.1021/acs.orglett.9b01372
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发表时间：
2019-06-07
期刊：
影响因子：
5.2
通讯作者：
Ando, Hiromune
中科院分区：
文献类型：
--
作者：
Asano, Sachi;Tanaka, Hide-Nori;Ando, Hiromune
芳香保护基由于其诸多优点在碳水化合物合成中得到了广泛的应用。然而，由于它们的pi堆叠能力，它们不可预测地使某些化合物不溶于有机溶剂。研究发现，在芳基上引入叔丁基可以提高高不溶性碳水化合物衍生物的溶解度，如n -乙酰氨基葡萄糖。在本研究中，叔丁基取代的芳香保护基团被证明与原始的未取代形式一样有效，同时提高了糖基化的效率。
Aromatic protective groups are widely used in carbohydrate synthesis owing to their numerous merits. However, they unpredictably make certain compounds insoluble in organic solvents owing to their pi-stacking abilities. It was found that introducing a tert-butyl group onto the aryl moiety improves the solubility of highly insoluble carbohydrate derivatives, such as those of N-acetylglucosamine. In this study, tert-butyl-substituted aromatic protecting groups are demonstrated to work as well as the original unsubstituted form, while improving the efficiency of glycosylations.