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The first synthesis of peracetyl glycosyl aurone derivatives and aurone glucosides
Tetrahedron ( IF 2.1 ) Pub Date : 2020-08-26 , DOI: 10.1016/j.tet.2020.131528
Arjun Kafle , Shrijana Bhattarai , Scott T. Handy

Aurones, a sub-class of the flavonoids with proven therapeutic importance, also exist in variously glycosylated forms. Although a large number of glycosylated aurone derivatives have been isolated from plant sources, no syntheses have been reported yet. Inspired from this gap, here we report the first synthesis of peracetylated glycosyl derivatives of synthetic aurones. The direct O-glycosylation was achieved by reacting 6-hydroxy aurones with 2, 3, 4, 6-tetra-O-acetyl-α-D glucopyranosyl bromide in the presence of a phase transfer catalyst tetrabutylammonium bromide (TBAB). The successful synthesis of aurone glycosides (33 examples) in 60–92% yield will benefit the synthesis of combinatorial libraries of glycosylated aurones for their biological study and comparison with non-glycosylated aurones.



中文翻译:

过乙酰基糖基金红酮衍生物和金红葡糖苷的首次合成

证明具有重要治疗意义的类黄酮类金盏花也以各种糖基化形式存在。尽管已从植物来源中分离出大量糖基化的金酮衍生物,但尚未报道合成方法。从这种差距中得到启发,在这里我们报告了合成金黄色素的全乙酰化糖基衍生物的首次合成。直接的O-糖基化是通过使6-羟基金氧烷与2、3、4、6-四-O-乙酰基反应而实现的-D吡喃葡萄糖基溴化物在相转移催化剂四丁基溴化铵(TBAB)的存在下。以60-92%的产率成功合成金酮糖苷(33个实例)将有益于糖基化金酮组合库的合成,以用于生物学研究和与非糖基化金酮的比较。

更新日期:2020-10-06
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