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

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摘要 A stereo-selective palladium-catalyzed one-pot Tsuji-Trost reaction was used to prepare four β-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 6a (C21H24O4S): orthorhombic system, space group P212121, a = 9.0919(4), b = 9.6313(4), c = 22.5936(11) Å, V = 1978.45(15) Å3, Z = 4, F(000) = 792, Dc = 1.250 g/cm3, 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 IC50 values of 69~88 μM.

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	焦阳
	张家鼎
	王树章
	姚辉
	刘明国
	黄年玉

关键词 ： X-ray diffraction, crystal structure, absolute configuration, β-thiogalactoside, cytotoxity

Abstract：A stereo-selective palladium-catalyzed one-pot Tsuji-Trost reaction was used to prepare four β-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 6a (C21H24O4S): orthorhombic system, space group P212121, a = 9.0919(4), b = 9.6313(4), c = 22.5936(11) Å, V = 1978.45(15) Å3, Z = 4, F(000) = 792, Dc = 1.250 g/cm3, 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 IC50 values of 69~88 μM.

Key words： X-ray diffraction crystal structure absolute configuration β-thiogalactoside cytotoxity

收稿日期: 2021-01-28 出版日期: 2021-09-09

基金资助:This project was supported by the National Natural Science Foundation of China (No. 82003621),Natural Science Foundation of Hubei Province (2020CFB205) and Educational Commission of Hubei Province (Q20201204)

通讯作者: mgliu1966@163.com E-mail: mgliu1966@163.com

引用本文:

焦阳;张家鼎;王树章;姚辉;刘明国;黄年玉. Synthesis and Absolute Configuration of ((2R,3R,6S)-3-Hydroxy-6-(naphthalen-2-ylthio)-3,6-dihydro-2H-pyran-2-yl)methyl Pivalate[J]. 结构化学, 2021, 40(9): 1238-1245.
JIAO Yang;ZHANG Jia-Ding;WANG Shu-Zhang;YAO Hui;LIU Ming-Guo;HUANG Nian-Yu. Synthesis and Absolute Configuration of ((2R,3R,6S)-3-Hydroxy-6-(naphthalen-2-ylthio)-3,6-dihydro-2H-pyran-2-yl)methyl Pivalate. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2021, 40(9): 1238-1245.

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