Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India.
Org Biomol Chem. 2020 May 6;18(17):3216-3228. doi: 10.1039/d0ob00297f.
l-Rhamnose forms the key components of important antigenic oligo- and polysaccharides of a variety of pathogens. Obtaining 1,2-cis stereoselectivity in the glycosylation of l-rhamnoside is quite challenging due to the unavailability of neighboring group participation and disfavoring of the anomeric effect and stereoelectronic effect of the substituents on the C-2 axial position. Nevertheless, various methodologies have been developed exploiting diverse pathways for obtaining β-stereoselectivity in the glycosylation of l-rhamnose. This review describes the recent advances in β-l-rhamnosylation and its applications in the total synthesis of β-l-rhamnose-containing biologically important oligosaccharides.
L-鼠李糖是多种病原体重要抗原性寡糖和多糖的关键组成部分。由于缺乏邻基参与以及不利于 C-2 轴向位置上取代基的端基效应和立体电子效应，因此在 l-鼠李糖苷的糖基化中获得 1,2-顺式立体选择性极具挑战性。尽管如此，人们还是开发了各种方法，利用不同的途径在 l-鼠李糖的糖基化中获得β-立体选择性。本文综述了近年来β-L-鼠李糖化及其在含有β-L-鼠李糖的生物重要寡糖全合成中的应用的最新进展。
