1219934-82-3Relevant academic research and scientific papers
Gold(I)-Catalyzed glycosylation with glycosyl ortho-alkynylbenzoates as donors: General scope and application in the synthesis of a cyclic triterpene saponin
Li, Yao,Yang, Xiaoyu,Liu, Yunpeng,Zhu, Cunsheng,Yang, You,Yu, Biao
supporting information; experimental part, p. 1871 - 1882 (2010/06/20)
Glycosyl ortho-alkynylbenzoates have emerged as a new generation of donors for glycosidation under the catalysis of gold(I) complexes such as Ph 3PAuOTf and Ph3PAuNTf2 (Tf= trifluoromethanesulfonate). A wide variety of these donors, including 2-deoxy sugar and sialyl donors, are easily prepared and shelf stable. The glycosidic coupling yields with alcohols are gener-ally excellent; even direct coupling with the poorly nucleophilic amides gives satisfactory yields. Moreover, excellent α-selective glycosylation with a 2-deoxy sugar donor and β-selective sialylation have been realized. Application of the present glycosylation protocol in the efficient synthesis of a cyclic triterpene tetrasaccharide have further demonstrated the versatility and efficacy of this new method, in that a novel chemoselective glycosylation of the carboxylic acid and a new one-pot sequential glycosylation sequence have been implemented.
