posted on 2024-03-13, 16:08authored byShuangyuan Chen, Feifei Wei, Xinqiang Cheng, Ying Luo, Fancui Meng, Yuanwen Zhang, Wenqian Huang, Jun Lv, Hong Pan, Qingqing Wu, Guilong Zhao
A general
approach for regioselective deacetylation at sugar 3-OH
of peracetylated 6-deoxy-C-glucopyranosides mediated
by BCl3 was developed. The approach could be extended to
other sugar-derived 6-deoxy-C-glycopyranosides, such
as those derived from mannose, galactose, and rhamnose, with deacetylation
occurring at varied sugar hydroxyl groups, and further extended to
4-deoxy-C-glucopyranosides with deacetylation occurring
at sugar 3-OH. The approach would enable access to synthetically challenging
carbohydrate derivatives. A possible mechanism of the regioselectivity
was proposed.