Ali Stacy P, Jalsa Nigel Kevin
Department of Chemistry, The University of the West Indies, St. Augustine, Trinidad and Tobago.
Department of Chemistry, The University of the West Indies, St. Augustine, Trinidad and Tobago.
Carbohydr Res. 2016 Feb;420:13-22. doi: 10.1016/j.carres.2015.11.007. Epub 2015 Dec 9.
The 2-N,N-dibenzylamino glucopyranosyl trichloroacetimidate donor was synthesized and an extensive investigation of its glycosyl donor properties was conducted. Coupling studies incorporated a variety of glycosyl promoters and a range of acceptor alcohols representing different reactivities and protecting group patterns. Various reaction temperatures, solvents and glycosylation protocols were also examined. Exclusive β-stereoselectivity was obtained in moderate to good yields with eight novel glycosides being produced, by probable neighbouring group participation via the formation of an aziridinium ion intermediate. Plausible reaction mechanisms were proposed based on the results obtained.
合成了2-N，N-二苄基氨基吡喃葡萄糖基三氯乙酰亚胺酯供体，并对其糖基供体性质进行了广泛研究。偶联研究纳入了多种糖基促进剂和一系列代表不同反应性和保护基模式的受体醇。还考察了各种反应温度、溶剂和糖基化方案。通过可能的邻基参与形成氮丙啶离子中间体，以中等至良好的产率获得了专一的β-立体选择性，生成了8种新型糖苷。根据所得结果提出了合理的反应机理。
