Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 Avenue de la Terrasse, 91190 Gif-sur-Yvette, France.
Org Lett. 2012 Mar 2;14(5):1342-5. doi: 10.1021/ol300255q. Epub 2012 Feb 15.
5-N-Acetyl-5-N,4-O-oxazolidinone protected α- and β-sialyl phosphates react with allyltributylstannane and a variety of trimethylsilyl enol ethers to give α-sialyl C-glycosides in high yield and excellent selectivity. Elimination to give the 2,3-glycal is minimized by the presence of the oxazolidinone ring. The oxazolidinone ring can be subsequently cleaved under mild conditions at room temperature leaving in place the native acetamide group.
5-N-乙酰基-5-N,4-O-噁唑烷酮保护的α-和β-唾液酸磷酸酯与烯丙基三丁基锡和各种三甲基硅基烯醇醚反应，以高产率和优异的选择性得到α-唾液酸 C-糖苷。由于噁唑烷酮环的存在，最大限度地减少了消除生成 2,3-糖苷醛的反应。噁唑烷酮环可以在温和条件下在室温下轻易地断裂，同时保留原始的乙酰胺基团。
