Discovery Sciences, Janssen Research & Development, Johnson & Johnson, Spring House, Pennsylvania 19477, United States.
Org Lett. 2020 Jul 17;22(14):5577-5581. doi: 10.1021/acs.orglett.0c01941. Epub 2020 Jul 6.
Transglycosylation of pyrimidine nucleosides is demonstrated in a one-pot synthesis of uridine derivatives under microwave irradiation. Inductive activation of 2',3',5'-tri--acetyl uridine with a 5-nitro group produces a more-reactive glycosyl donor. Under optimized Vorbrüggen conditions, the 5-nitrouridine facilitates a reversible nucleobase exchange with a series of 5-substituted uracils. The protocol is also exemplified in a gram-scale reaction under thermal heating. The strategy provides easy access to isotopically labeled uridine.
在微波辐射下一锅合成尿嘧啶衍生物的过程中证明了嘧啶核苷的转糖基化。用 5-硝基基团诱导激活 2',3',5'-三--乙酰尿苷，产生更具反应性的糖苷供体。在优化的 Vorbrüggen 条件下，5-硝基尿嘧啶促进与一系列 5-取代的尿嘧啶的可逆核碱基交换。该方案也在热加热下的克级反应中得到了例证。该策略为同位素标记的尿嘧啶提供了便捷的获取途径。
