Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Huazhong University of Science and Technology, 13 Hangkong Road, Wuhan, Hubei 430030, People's Republic of China.
Institute of Brain Research, Huazhong University of Science and Technology, 13 Hangkong Road, Wuhan, Hubei 430030, People's Republic of China.
J Am Chem Soc. 2020 Mar 25;142(12):5498-5503. doi: 10.1021/jacs.0c00447. Epub 2020 Mar 13.
A novel one-pot relay glycosylation has been established. The protocol is characterized by the construction of two glycosidic bonds with only one equivalent of triflic anhydride. This method capitalizes on the generated cyclic-thiosulfonium ion as the relay activator, which directly activates the newly formed thioglycoside in one pot. A wide range of substrates are well-accommodated to furnish both linear and branched oligosaccharides. The synthetic utility and advantage of this method have been demonstrated by rapid access to naturally occurring phenylethanoid glycoside kankanoside F and resin glycoside merremoside D.
建立了一种新颖的一锅法接力糖苷化反应。该方法的特点是仅使用一当量的三氟甲磺酸酐构建两个糖苷键。该方法利用生成的环状硫代磺酸离子作为接力活化剂，在一锅反应中直接激活新形成的硫糖苷。广泛的底物都能很好地适应，从而得到线性和支化的寡糖。通过快速合成天然苯乙醇苷坎卡诺苷 F 和树脂苷梅雷莫苷 D，证明了该方法的合成实用性和优势。
