5-核糖或木糖亚甲基-2,4-咪唑啉二酮衍生物的合成及其杀菌活性
收稿日期: 2014-01-21
修回日期: 2014-03-05
网络出版日期: 2014-04-15
基金资助
“十二五”科技支撑计划（No.2011BAE06B03）资助项目.
Synthesis and Fungicidal Activity of D-Ribose and D-Xylose with Hydantion
Received date: 2014-01-21
Revised date: 2014-03-05
Online published: 2014-04-15
Supported by
Project supported by the National Key Technologies R&D Program (No. 2011BAE06B03).
以1，2：5，6-O-二异丙叉-α-D-呋喃葡萄糖为原料，经过吡啶重铬酸盐（PDC）氧化、NaBH4还原及选择性水解，实现α-D-木糖环向α-D-核糖环的C（3）位羟基构型的转化，然后分别在高碘酸钠氧化作用下得到糖环上C（5）位为醛基的α-D-木糖和α-D-核糖衍生物，它们分别与2，4-咪唑啉二酮-5-膦酸酯及2-硫代-2，4-咪唑啉二酮发生Wittig-Horner反应及Knoevenagel反应，分离得到3对5-核糖或木糖亚甲基-2，4-咪唑啉二酮衍生物顺反异构体，它们的化学结构经1H NMR，IR，MS和X射线单晶衍射确证. 初步生物活性测定结果表明： 在50 μg/mL浓度下，部分目标化合物均对供试菌种显现出一定的抑制活性.
刘斌 , 韩金涛 , 汤博 , 王明安 . 5-核糖或木糖亚甲基-2,4-咪唑啉二酮衍生物的合成及其杀菌活性[J]. 有机化学, 2014 , 34(7) : 1442 -1446 . DOI: 10.6023/cjoc201401035
The α-D-ribose and α-D-xylose C(5)-aldehyde derivatives (1 and 2) were prepared through four and two steps using 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose as raw material. Then 1 and 2 reacted with hydantoin phosphonate and 2-thiohydantoin by Wittig-Horner and Knoevenagel reaction to afford 3 pairs of E and Z isomers of target products 3～5. Their structures were elucidated by 1H NMR, 13C NMR, IR, MS and X-ray diffraction. The preliminary bioassay results showed that some of them have certain fungicidal activities against 7 plant pathogens at the concentration of 50 μg/mL.
Key words： hydantoin; ribose; xylose; fungicidal activity
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