Efficient one-pot synthesis of 2-hydroxyethyl per-O-acetyl glycosides |
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| Authors: | Hong-Wen Tao Xia Wang Ping-Gui Yi Zhi-Hong Deng Xian-Yong Yu Xiao-Fang Li |
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| Affiliation: | 1. Key Laboratory of Theoretical Chemistry and Molecular Simulation of the Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, 411201, China
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| Abstract: | A class of stereo-isomerically-pure alkanediol monoglycosides, 2-hydroxyethyl per-O-acetyl pyranosides (IIIa-IIIf), was conveniently prepared by a one-pot reaction of per-O-acetylated pyranoses (Ia-If) and 2-(tert-butyldimethylsilyloxy)ethanol (II) with catalysis by BF3·OEt2. The α-(IIIa) or β-linked glycosides (IIIb-IIIf) with 1,2-trans-configuration were obtained from glycosyl donors with participation of the neighbouring 2-O-acetyl group. BF3·OEt2, along with hydrogen fluoride released from BF3·OEt2 under the experimental conditions used, facilitates the subsequent de-protection of siloxane to successfully afford 2-hydroxyethyl per-O-acetyl-pyranosides. |
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