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  

Synthesis and Fungicidal Activity of D-Ribose and D-Xylose with Hydantion

作　　者：刘斌[1] 韩金涛[1] 汤博[1] 王明安[1] 

机构地区：[1]中国农业大学应用化学系,北京100193

出　　处：《有机化学》2014年第7期1442-1446,共5页Chinese Journal of Organic Chemistry

基　　金："十二五"科技支撑计划(No.2011BAE06B03)资助项目~~

摘　　要：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50μg/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.The α-D-ribose and a-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-Homer 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.

关 键 词：2 4-咪唑啉二酮 木糖 核糖 杀菌活性 

分 类 号：TQ455[化学工程—农药化工]