1448014-17-2Relevant academic research and scientific papers
Highly efficient α-C-sialylation promoted by (p-Tol) 2SO/Tf2O with N-acetyl-5-N,4-O-oxazolidione protected thiosialoside as donor
Gu, Zhen-Yuan,Zhang, Xiao-Tai,Zhang, Jia-Xin,Xing, Guo-Wen
, p. 5017 - 5022 (2013)
Based on a preactivation protocol with (p-Tol)2SO/Tf 2O, a practical, straightforward, and high-yielding synthesis of α-sialyl C-glycosides was accomplished by coupling N-acetyl-5-N,4-O- oxazolidione protected thiosialoside with various trimethylsilyl enol ethers and allyltrimethylsilanes. High yields and excellent α-selectivities were obtained for the strong π-nucleophiles with large nucleophilicity values (N = 4.4-9.0), irrespective of whether silyl enol ethers, silyl ketene acetals or allyltrimethylsilanes were used for the electrophilic C-sialylation.
