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Efficient one-pot synthesis of 2-hydroxyethyl per-O-acetyl glycosides

Hong-Wen Tao, Xia Wang, Ping-Gui Yi, Zhi-Hong Deng, Xian-Yong Yu, and Xiao-Fang Li

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

 

E-mail: pgyi@hnust.edu.cn

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.

Keywords: one-pot synthesis – alkanediol monoglycoside – glycosylation – neighbouring group participation

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-014-0552-8

 

Chemical Papers 68 (8) 1132–1136 (2014)

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