Das Anupama, Adio Shay, Brincken Jeremy, Demchenko Alexei V, De Meo Cristina
Department of Chemistry, Saint Louis University, 3501 Laclede Ave, St. Louis, MO, 63103, USA.
Department of Chemistry, Southern Illinois University Edwardsville, Edwardsville, IL, 62026, USA.
Carbohydr Res. 2025 Feb;548:109353. doi: 10.1016/j.carres.2024.109353. Epub 2024 Dec 13.
With the expanding use of phosphates as leaving groups in sialylations, little remains known about the C-5 effect towards their reactivity and stereoselectivity in the presence of a range of acceptors, and in different solvents. Herein we report the comparison between sialyl phosphate donors bearing N-acetyloxazolidinone and trifluoroacetamido functionalities at C-5. Excellent results and complete stereoselectivity were observed in several sialylations, but the outcome was influenced by the nature of the solvent and/or glycosyl acceptor.
随着磷酸酯作为唾液酸化反应中离去基团的应用不断扩大，在一系列受体存在以及不同溶剂中，关于C-5对其反应活性和立体选择性的影响仍知之甚少。在此，我们报道了在C-5位带有N-乙酰基恶唑烷酮和三氟乙酰胺官能团的唾液酸磷酸供体之间的比较。在多个唾液酸化反应中观察到了优异的结果和完全的立体选择性，但结果受到溶剂性质和/或糖基受体的影响。
