在弱亲核环境中由4-酯基介导的β-L-鼠李糖基化和β-D-甘露糖基化
β-l-Rhamnosylation and β-d-Mannosylation Mediated by 4--Ester Groups in a Weakly Nucleophilic Environment.
作者信息
Zhang Yongliang, Chen Changsheng, Gao Yongtao, Yang Min, He Zehuan, Zhang Bangzhi, Gu Guofeng, Tang Bencan, Cai Feng
机构信息
National Glycoengineering Research Center and Shandong Key laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 72 Binhai Rd Qingdao 266237, China.
Center for Analysis and Characterization, School of Physical Science and Technology, ShanghaiTech University, 393 Huaxia Middle Rd, Shanghai 201210, China.
出版信息
Org Lett. 2023 Oct 6;25(39):7120-7125. doi: 10.1021/acs.orglett.3c02566. Epub 2023 Sep 22.
-4--Acyl group directed β-rhamnosylation and β-mannosylation are achieved in a carborane or BARF anion formed weakly nucleophilic environment with the assistance of a 2,3-orthocarbonate group. The 4--acyl group plays a critical role in directing the β-selectivity, and the weakly coordinating anion is essential to amplify this direction. The orthocarbonate group could be readily removed with 1,3-propanediol in the presence of BF·EtO.
-4-酰基导向的β-鼠李糖基化和β-甘露糖基化反应是在碳硼烷或BARF阴离子形成的弱亲核环境中，借助2,3-原碳酸酯基团实现的。4-酰基在引导β-选择性方面起着关键作用，而弱配位阴离子对于增强这种导向作用至关重要。在BF·EtO存在的情况下，原碳酸酯基团可以很容易地用1,3-丙二醇除去。
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