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

Autor: Tao, Hong-Wen, Wang, Xia, Yi, Ping-Gui, Deng, Zhi-Hong, Yu, Xian-Yong, Li, Xiao-Fang
Zdroj: Chemical Papers; Aug2014, Vol. 68 Issue 8, p1132-1136, 5p
Abstrakt: 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 BF·OEt. 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. BF·OEt, along with hydrogen fluoride released from BF·OEt under the experimental conditions used, facilitates the subsequent de-protection of siloxane to successfully afford 2-hydroxyethyl per- O-acetyl-pyranosides. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index