Synthesis and Absolute Configuration of((2R,3R,6S)-3-Hydroxy-6-(naphthalen-2-ylthio)-3,6-dihydro-2H-pyran-2-yl)methyl Pivalate  

作　　者：JIAO Yang ZHANG Jia-Ding WANG Shu-Zhang YAO Hui LIU Ming-Guo HUANG Nian-Yu 焦阳;张家鼎;王树章;姚辉;刘明国;黄年玉(Hubei Key Laboratory of Natural Products Research and Development,Key Laboratory of Functional Yeast(China National Light Industry),College of Biological and Pharmaceutical Sciences,China Three Gorges University,Tichang 443002,China)

机构地区：[1]Hubei Key Laboratory of Natural Products Research and Development,Key Laboratory of Functional Yeast(China National Light Industry),College of Biological and Pharmaceutical Sciences,China Three Gorges University,Tichang 443002,China

出　　处：《Chinese Journal of Structural Chemistry》2021年第9期1238-1245,1112,共9页结构化学（英文）

基　　金：the National Natural Science Foundation of China(No.82003621);Natural Science Foundation of Hubei Province(2020CFB205);Educational Commission of Hubei Province(Q20201204)。

摘　　要：A stereo-selective palladium-catalyzed one-pot Tsuji-Trost reaction was used to prepare fourβ-thiogalactosides from unsaturated D-galactal and thiol.Their structures were characterized by nuclear magnetic resonance spectra and high-resolution electrospray ionization mass spectra.The absolute configuration was confirmed with a Flack parameter of 0.019(15)by X-ray crystallography using a Cu radiation source.Compound 6 a(C_(21)H_(24)O_(4)S):orthorhombic system,space group P2_(1)2_(1)2_(1),a=9.0919(4),b=9.6313(4),c=22.5936(11)A,V=1978.45(15)A^(3),Z=4,F(000)=792,D_(c)=1.250 g/cm^(3),μ=1.636 mm^(-1),R=0.0478 and wR=0.1384 for 3621 independent reflections(Rint=0.0390)and 3326 observed ones(I>2σ(I)).3-(4,5)-Dimethylthiazol-2-yl-2,5-diphenyltetrazolium bromide(MTT)cell viability assays indicated that these thiogalactosides showed anti-proliferative activities against human gastric cancer HGC-27 cells with IC_(50)values of 69~88μM.

关 键 词：X-ray diffraction crystal structure absolute configuration β-thiogalactoside CYTOTOXITY 

分 类 号：TQ460.1[化学工程—制药化工]