Citation: Yang JIAO, Jia-Ding ZHANG, Shu-Zhang WANG, Hui YAO, Ming-Guo LIU, Nian-Yu HUANG. Synthesis and Absolute Configuration of ((2R, 3R, 6S)-3-Hydroxy-6-(naphthalen-2-ylthio)-3, 6-dihydro-2H-pyran-2-yl)methyl Pivalate[J]. Chinese Journal of Structural Chemistry, ;2021, 40(9): 1238-1245. doi: 10.14102/j.cnki.0254–5861.2011–3124 shu

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

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, Yichang 443002, China

Corresponding author: Ming-Guo LIU, mgliu1966@163.com Nian-Yu HUANG, huangny@ctgu.edu.cn
Received Date: 28 January 2021
Accepted Date: 13 April 2021

Fund Project: the National Natural Science Foundation of China 82003621Natural Science Foundation of Hubei Province 2020CFB205Educational Commission of Hubei Province Q20201204

Figures(3)

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, D_c = 1.250 g/cm³, μ = 1.636 mm⁻¹, R = 0.0478 and wR = 0.1384 for 3621 independent reflections (R_int = 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.
- X-ray diffraction,
- crystal structure,
- absolute configuration,
- β-thiogalactoside,
- cytotoxity
1. [1]
  Damaraju, V. L.; Damaraju, S.; Young, J. D.; Baldwin, S. A.; Mackey, J.; Sawyer, M. B.; Cass, C. E. Nucleoside anticancer drugs: the role of nucleoside transporters in resistance to cancer chemotherapy. Oncogene 2003, 22, 7524–7536. doi: 10.1038/sj.onc.1206952
2. [2]
  Seley-Radtke, K. L.; Yates, M. K. The evolution of nucleoside analogue antivirals: a review for chemists and non-chemists. Part 1: early structural modifications to the nucleoside scaffold. Antiviral Res. 2018, 154, 66–86. doi: 10.1016/j.antiviral.2018.04.004
3. [3]
  Osada, H. Discovery and applications of nucleoside antibiotics beyond polyoxin. J. Antibiot. 2019, 72, 855–864. doi: 10.1038/s41429-019-0237-1
4. [4]
  Feng, M.; Tang, B.; Liang, S. H.; Jiang, X. Sulfur containing scaffolds in drugs: synthesis and application in medicinal chemistry. Curr. Top. Med. Chem. 2016, 16, 1200–1216. doi: 10.2174/1568026615666150915111741
5. [5]
  Wright, A. J. The penicillins. Mayo Clin. Proc. 1999, 74, 290–307. doi: 10.4065/74.3.290
6. [6]
  Vicente, D.; Pérez-Trallero, E. Tetracyclines, sulfonamides, and metronidazole. Enferm. Infecc. Microbiol. Clin. 2010, 28, 122–130. doi: 10.1016/j.eimc.2009.10.002
7. [7]
  Pan, C.; Kuranaga, T.; Kakeya, H. Total synthesis of thioamycolamide A via a biomimetic route. Org. Biomol. Chem. 2020, 18, 8366–8370. doi: 10.1039/D0OB01942A
8. [8]
  Kobayashi, E.; Motoki, K.; Uchida, T.; Fukushima, H.; Koezuka, Y. KRN7000, a novel immunomodulator, and its antitumor activities. Oncol. Res. 1995, 7, 529–534.
9. [9]
  Zhang, L.; Carthy, C. M.; Zhu, X. Synthesis of a glucosylated alpha-S-galactosylceramide as potential immunostimulant. Carbohydr. Res. 2017, 448, 43–47. doi: 10.1016/j.carres.2017.05.022
10. [10]
  Lian, G.; Zhang, X.; Yu, B. Thioglycosides in carbohydrate research. Carbohydr. Res. 2015, 403, 13–22. doi: 10.1016/j.carres.2014.06.009
11. [11]
  Codée, J. D.; Litjens, R. E.; van den Bos, L. J.; Overkleeft, H. S.; van der Marel, G. A. Thioglycosides in sequential glycosylation strategies. Chem. Soc. Rev. 2005, 34, 769–782. doi: 10.1039/b417138c
12. [12]
  Zhu, F.; Miller, E.; Zhang, S. Q.; Yi, D.; O'Neill, S.; Hong, X.; Walczak, M. A. Stereoretentive C(sp³)-S cross-coupling. J. Am. Chem. Soc. 2018, 140, 18140–18150. doi: 10.1021/jacs.8b11211
13. [13]
  Zhu, M.; Alami, M.; Messaoudi, S. Electrochemical nickel-catalyzed Migita cross-coupling of 1-thiosugars with aryl, alkenyl and alkynyl bromides. Chem. Commun. 2020, 56, 4464–4467. doi: 10.1039/D0CC01126F
14. [14]
  Procopio, A.; Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Nardi, M.; Oliverio, M.; Russo, B. A facile Er(OTf)₃-catalyzed synthesis of 2, 3-unsaturated O- and S-glycosides. Carbohydr. Res. 2007, 342, 2125–2131. doi: 10.1016/j.carres.2007.05.034
15. [15]
  Stevanović, D.; Pejović, A.; Damljanović, I.; Minić, A.; Bogdanović, G. A.; Vukićević, M.; Radulović, N. S.; Vukićević, R. D. Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst. Carbohydr. Res. 2015, 407, 111–121. doi: 10.1016/j.carres.2015.02.001
16. [16]
  Meng, S.; Zhong, W.; Yao, W.; Li, Z. Stereoselective phenylselenoglycosylation of glycals bearing a fused carbonate moiety toward the synthesis of 2-deoxy-β-galactosides and β-mannosides. Org. Lett. 2020, 22, 2981–2986. doi: 10.1021/acs.orglett.0c00732
17. [17]
  Lai, M. N.; Abdulmajed Othman, K.; Yao, H.; Wang, Q. Y.; Feng, Y. K.; Huang, N. Y.; Liu, M. G.; Zou, K. Open-air stereoselective construction of C-aryl glycosides. Org. Lett. 2020, 22, 1144–1148. doi: 10.1021/acs.orglett.9b04665
18. [18]
  Sheldrick, G. M. SHELXL 97, Program for Crystal Structure Determinations. University of Göttingen, Germany 1997.
19. [19]
  Sheldrick, G. M. SHELXL 97, Program for the Refinement of Crystal Structure. University of Göttingen, Germany 1997.
20. [20]
  Pascua-Maestro, R.; Corraliza-Gomez, M.; Diez-Hermano, S.; Perez-Segurado, C.; Ganfornina, M. D.; Sanchez, D. The MTT-formazan assay: complementary technical approaches and in vivo validation in Drosophila larvae. Acta Histochem. 2018, 120, 179–186. doi: 10.1016/j.acthis.2018.01.006
21. [21]
  Rose, J. D.; Parker, W. B.; Someya, H.; Shaddix, S. C.; Montgomery, J. A.; Secrist, J. A. Enhancement of nucleoside cytotoxicity through nucleotide prodrugs. J. Med. Chem. 2002, 45, 4505–4512. doi: 10.1021/jm020107s
22. [22]
  MacMillan, J. B.; Guang, X. Z.; Skepper, C. K.; Molinski, T. F. Phorbasides A−E, cytotoxic chlorocyclopropane macrolide glycosides from the marine sponge Phorbas sp. CD determination of C-methyl sugar configurations. J. Org. Chem. 2008, 73, 3699–3706. doi: 10.1021/jo702307t
23. [23]
  Ogunsina, M.; Samadder, P.; Idowu, T.; Arthur, G.; Schweizer, F. Replacing D-glucosamine with its l-enantiomer in glycosylated antitumor ether lipids (GAELs) retains cytotoxic effects against epithelial cancer cells and cancer stem cells. J. Med. Chem. 2017, 60, 2142–2147. doi: 10.1021/acs.jmedchem.6b01773
24. [24]
  Paolini, J. P. The bond order-bond length relationship. J. Comput. Chem. 1990, 11, 1160–1163. doi: 10.1002/jcc.540111007
25. [25]
  Cao, C. Q.; Yan, X. M.; Yang, Q. L.; Luo, H. J.; Huang, N. Y. Synthesis and crystal structure of (Z)-2-methyl-5, 6-dihydrobenzo[d]thiazol-7(4H)-one O-prop-2-yn-1-yl oxime derivatives. Chin. J. Struc. Chem. 2014, 33, 1683−1688.
26. [26]
  Lu, X. F.; Yang, Z.; Huang, N. Y.; He, H. B.; Deng, W. Q.; Zou, K. Synthesis and cytotoxic activities of 2-substituted (25R)-spirostan-1, 4, 6-triene-3-ones via ring-opening/elimination and "click" strategy. Bioorg. Med. Chem. Lett. 2015, 25, 3726–3729. doi: 10.1016/j.bmcl.2015.06.028
27. [27]
  Yao, Y.; Xiong, C. P.; Zhong, Y. L.; Bian, G. W.; Huang, N. Y.; Wang, L.; Zou, K. Intramolecular and Ferrier rearrangement strategy for the construction of C1-β-D-xylopyranosides: synthesis, mechanism and biological activity study. Adv. Syn. Cat. 2019, 361, 1012–1017. doi: 10.1002/adsc.201801423
28. [28]
  Wang, Y.; Yao, H.; Hua, M.; Jiao, Y.; He, H. B.; Liu, M. G.; Huang, N. Y.; Zou, K. Direct N-glycosylation of amides/amines with glycal donors. J. Org. Chem. 2020, 85, 7485–7493. doi: 10.1021/acs.joc.0c00975
29. [29]
  West, B. T. Analyzing longitudinal data with the linear mixed models procedure in SPSS. Eval. Health Prof. 2009, 32, 207−228. doi: 10.1177/0163278709338554
1. [1]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
2. [2]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
3. [3]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
4. [4]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
5. [5]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
6. [6]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
7. [7]
  Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
8. [8]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
9. [9]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
10. [10]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
11. [11]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
12. [12]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
13. [13]
  Wei Li , Guoqiang Feng , Ze Chang . Teaching Reform of X-ray Diffraction Using Synchrotron Radiation in Materials Chemistry. University Chemistry, 2024, 39(3): 29-35. doi: 10.3866/PKU.DXHX202308060
14. [14]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
15. [15]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
16. [16]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
17. [17]
  Yinling HOU , Jia JI , Hong YU , Xiaoyun BIAN , Xiaofen GUAN , Jing QIU , Shuyi REN , Ming FANG . A rhombic Dy₄-based complex showing remarkable single-molecule magnet behavior. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 605-612. doi: 10.11862/CJIC.20240251
18. [18]
  Xin Dong , Tianqi Chen , Jing Liang , Lei Wang , Huajie Wu , Zhijin Xu , Junhua Luo , Li-Na Li . Structure design of lead-free chiral-polar perovskites for sensitive self-powered X-ray detection. Chinese Journal of Structural Chemistry, 2024, 43(6): 100256-100256. doi: 10.1016/j.cjsc.2024.100256
19. [19]
  Yan-Jiang Li , Shu-Lei Chou , Yao Xiao . Detecting dynamic structural evolution based on in-situ high-energy X-ray diffraction technology for sodium layered oxide cathodes. Chinese Chemical Letters, 2025, 36(2): 110389-. doi: 10.1016/j.cclet.2024.110389
20. [20]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(302)
HTML views(4)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142