Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar

doi:10.6023/cjoc202307001

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (2): 593-604.DOI: 10.6023/cjoc202307001 Previous Articles Next Articles

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1β-/3R-芳基硫代糖的区域与立体选择性合成

邹发凯, 王能中, 姚辉^*(), 王慧, 刘明国, 黄年玉^*()

三峡大学生物与制药学院天然产物研究与利用湖北省重点实验室中国轻工业功能酵母重点实验室湖北宜昌 443002

收稿日期:2023-07-01 修回日期:2023-09-26 发布日期:2023-10-23
基金资助:
国家自然科学基金(22207063); 高等学校学科创新引智计划(111 计划, No. D20015); 湖北省自然科学基金(2022CFB838); 及湖北省教育厅(D20221204); 及湖北省教育厅(Q20221212)

Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar

Fakai Zou, Nengzhong Wang, Hui Yao(), Hui Wang, Mingguo Liu, Nianyu Huang()

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, Hubei 443002

Received:2023-07-01 Revised:2023-09-26 Published:2023-10-23
Contact: * E-mail: yaohui@ctgu.edu.cn; huangny@ctgu.edu.cn
Supported by:
National Natural Science Foundation of China(22207063); Programme of Introducing Talent of Discipline to Universities(No. D20015); Natural Science Foundation of Hubei Province(2022CFB838); Educational Commission of Hubei Province(D20221204); Educational Commission of Hubei Province(Q20221212)

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Abstract

Thiosugars have attracted much attention in the field of pharmaceuticals because of their excellent biological activities, and chemical synthesis is an important way to obtain thiosugars. Using 6-O-diphenylphosphoryl-3,4-O-carbonate-D-gala- ctal and thiophenols as starting materials, the regio- and stereo-selective syntheses of 1β-/(3R)-aryl thiosugars were controlled with NiBr₂ and Pd₂(dba)₃ catalysts, respectively. The structures of the target compounds were characterized by nuclear magnetic resonance, high-resolution mass spectrometry and single crystal X-ray diffraction. This method exhibited favourable compatibility with various functional groups substituted thiophenols, which could be used for the structural modification of active natural products. The research work is help for the rapid construction of the compound library of 1β-/(3R)-aryl thiosugars for drug discovery.

Key words: Pd catalysis, Ni catalysis, D-galactal, thiosugar, synthesis

Cite this article

Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar[J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.

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References 41

[1]	Hu, J.; Lu, K.; Gu, C.; Heng, X.; Shan, F. J.; Chen, G. J. Biomacromolecule. 2022, 23, 1075. doi: 10.1021/acs.biomac.1c01409
[2]	Tyrikos-Ergas, T.; Fittolani, G.; Seeberger, P. H.; Delbinco, M. Biomacromolecule. 2019, 21, 18. doi: 10.1021/acs.biomac.9b01090
[3]	Ng, J. Y.; Tan, K. Y. F.; Ee, P. L. R. Biomacromolecule. 2022, 23, 2803. doi: 10.1021/acs.biomac.2c00176
[4]	Li, G. F.; Jing, J.; Luo, Z. Y.; Mo, J.; Xiong, D. C.; Ye, X. S. Chin. J. Org. Chem. 2023, 43, 1991 (in Chinese). doi: 10.6023/cjoc202211024
	(李格非, 荆杰, 罗振扬, 默娟, 熊德彩, 叶新山, 有机化学, 2023, 43, 1991.)
[5]	Morrone-Pozzuto, P.; Uhrig, M. L.; Agusti, R. J. Org. Chem. 2022, 87, 13455. doi: 10.1021/acs.joc.2c01059 pmid: 35775947
[6]	Wang, Q. Y.; Lai, M. N.; Luo, H. J.; Ren, K. K.; Wang, J. R.; Huang, N. Y.; Deng, Z. S.; Zou, K.; Yao, H. Org. Lett. 2022, 24, 1587. doi: 10.1021/acs.orglett.1c04378
[7]	Hou, M. Y.; Xiang, Y. M.; Gao, J. Y.; Zhang, J. Y.; Wang, N. Z.; Shi, H. L.; Huang, N. Y.; Yao, H. Org. Lett. 2023, 25, 832. doi: 10.1021/acs.orglett.2c04379
[8]	Qin, K.; Zhang, H.; Zhao, Z.; Chen, X. J. Am. Chem. Soc. 2020, 142, 9382. doi: 10.1021/jacs.0c02110 pmid: 32339456
[9]	Xiong, T.; Xie, R.; Huang, C.; Lan, X.; Huang, N. Y.; Yao, H. J. Carbohydr. Chem. 2021, 40, 401. doi: 10.1080/07328303.2022.2027433
[10]	Li, G.; Dao, Y.; Mo, J.; Dong, S. W.; Shoda, S.; Ye, X. S. CCS Chem. 2022, 4, 1930. doi: 10.31635/ccschem.021.202101115
[11]	Castaneda, F.; Burse, A.; Boland, W.; Kinne, R. K. Int. J. Med. Sci. 2007, 4, 131.
[12]	Zhang, J. J.; Cao, W.; Xi, P.; Li, L.; Qiao, S. T.; Luo, H. W.; Zhang, J. Y.; Liu, X. Y.; Du, N. S. J. Agric. Food Chem. 2021, 69, 12974. doi: 10.1021/acs.jafc.1c04725
[13]	Ding, X. L.; Kong, F. Z. Chin. J. Org. Chem. 2000, 20, 319 (in Chinese).
	(丁香兰, 孔繁祚, 有机化学, 2000, 20, 319.)
[14]	Liu, H.; Zhi, F.; Liu, H.; Liao, J.; Zhong, L.; Tu, Y.; Zhang, Q.; Xiong, B.; Sun, J. J. Am. Chem. Soc. 2023, 145, 3682. doi: 10.1021/jacs.2c13018
[15]	Marzo, T.; Cirri, D.; Gabbiani, C.; Gamberi, T.; Magherini, F.; Pratesi, A.; Guerri, A.; Biver, T.; Binacchi, F.; Stefanini, M.; Arcangeli, A.; Messori, L. ACS Med. Chem. Lett. 2017, 8, 997. doi: 10.1021/acsmedchemlett.7b00162
[16]	Epstein, T. D.; Wu, B.; Moulton K. D. Yan, M.; Dube, D. H. ACS Infect. Dis. 2019, 5, 1682. doi: 10.1021/acsinfecdis.9b00251 pmid: 31487153
[17]	Escrig, J. I.; Hahn, H. J.; Debnath, A. ACS Chem. Neurosci. 2020, 11, 2464. doi: 10.1021/acschemneuro.0c00165
[18]	Chevolleau, S.; Debrauwer, L.; Boyer, G.; Tulliez, J. J. Agric. Food Chem. 2002, 50, 5185. doi: 10.1021/jf020125i
[19]	Agneta, R.; Rivelli, A. R.; Ventrella, E.; Leario, F.; Sarli, G.; Bufo, S. A. J. Agric. Food Chem. 2012, 60, 7474. doi: 10.1021/jf301294h
[20]	Sun, J.; Kou, L.; Geng, P.; Huang, H.; Yang, T.; Luo, Y.; Chen, P. J. Agric. Food Chem. 2015, 63, 1863. doi: 10.1021/jf504710r
[21]	Birkenmeyer, R. D.; Kroll, S. J.; Lewis, C.; Stern, K. F.; Zurenko, G. E. J. Med. Chem. 1984, 27, 216. pmid: 6363698
[22]	Ding, C.; Bremer, N. M.; Smith, T. D.; Seitz, P. K.; Anastasio, N. C.; Cunningham, K. A.; Zhou, J. ACS Chem. Neurosci. 2012, 3, 538. doi: 10.1021/cn300020x
[23]	Guo, Z.; Bai, J.; Liu, M.; Xiong, D.; Ye, X. Chin. J. Org. Chem. 2020, 40, 3094 (in Chinese). doi: 10.6023/cjoc202006005
	(郭真言, 柏金和, 刘苗, 熊德彩, 叶新山, 有机化学, 2020, 40, 3094.)
[24]	Ji, P.; Zhang, Y.; Gao, F.; Bi, F.; Wang, W. Chem. Sci. 2020, 11, 13079. doi: 10.1039/D0SC04136J
[25]	Liu, J.; Zhang, G. Chin. J. Org. Chem. 2009, 29, 1890 (in Chinese).
	(刘青锋, 张贵生, 有机化学, 2009, 29, 1890.)
[26]	Sarkar, B.; Pramanik, T.; Jayaraman, N. J. Org. Chem. 2023, 88, 607.
[27]	Li, X.; Zhu, J. Eur. J. Org. Chem. 2016, 2016, 4724. doi: 10.1002/ejoc.v2016.28
[28]	Wan, Y.; Deng, L.; Tu, Y.; Liu, H.; Sun, J.; Zhang, Q. Chin. J. Chem. Eng. 2023, 41, 2837.
[29]	Zhang, G.; Gadi, M.; Cui, X.; Liu, D.; Zhang, J.; Saikam, V.; Gibbons, C.; Wang, P.; Li, L. Green Chem. 2021, 23, 2907. doi: 10.1039/D1GC00098E
[30]	Wang, Y.; Cao, Z.; Wang, N.; Liu, M.; Zhou, H.; Wang, L.; Huang, N. Adv. Synth. Catal. 2023, 365, 1699. doi: 10.1002/adsc.v365.10
[31]	Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596. doi: 10.1021/cr100347k pmid: 21391564
[32]	Li, J.; Wang, M.; Jiang, X. Org. Lett. 2021, 23, 9053. doi: 10.1021/acs.orglett.1c03302
[33]	Liu, Y.; Jiao, Y.; Luo, H. J.; Huang, N. Y.; Lai, M. N.; Zou, K.; Yao, H. ACS Catal. 2021, 11, 5287. doi: 10.1021/acscatal.1c00225
[34]	Jiao, Y.; Zhang, J.; Wang, S.; Yao H. ; Liu, M.; Huang, N. Chin. J. Struct. Chem. 2021, 40, 1238.
[35]	Yao, H.; Zhang, S.; Leng, W. L.; Leow, M. L.; Xiang, S. H.; He, J. X.; Liao, H. Z.; Hoang, K. L. M.; Liu, X. W. ACS Catal. 2017, 7, 5456. doi: 10.1021/acscatal.7b01630
[36]	Hua, M.; Sun, Y. X.; Zhang, X. Q.; Huang, N. Y.; Yao, H. Chin. J. Org. Chem. 2022, 42, 2140 (in Chinese). doi: 10.6023/cjoc202202021
	(华敏, 孙阳星, 张雪晴, 黄年玉, 姚辉, 有机化学, 2022, 42, 2140.)
[37]	Guerrero, G.; Mutin, P. H.; Vioux, A. Chem. Mater. 2001, 13, 4367. doi: 10.1021/cm001253u
[38]	Hoogenband, A.; Lange, J. H. M.; Bronger, R. P. J.; Stoit, A. R.; Terpstra, J. Tetrahedron Lett. W. 2010, 51, 6877. doi: 10.1016/j.tetlet.2010.10.125
[39]	You, X.; Cai, Y.; Xiao, C.; Ma, L.; Wei, Y.; Xie, T.; Chen, L.; Yao, H. Molecule. 2022, 27, 7979. doi: 10.3390/molecules27227979
[40]	Shang, W.; Shi, R.; Niu, D. Chin. J. Chem. 2023, 17, 2217.
[41]	Liu, X.; Lin, Y.; Liu, A.; Sun, Q.; Sun, H.; Xu, P.; Li, G.; Song, Y.; Xie, W.; Sun, H.; Yu, B.; Li, W. Chin. J. Chem. 2022, 40, 443. doi: 10.1002/cjoc.v40.4

Entry	Catalyst	Ligand	Solvent	Yield^c/%
1	PdCl₂	Xantphos	CH₂Cl₂	N.R.
2	Pd(PPh₃)₄	Xantphos	CH₂Cl₂	N.R.
3	Pd(OAc)₂	Xantphos	CH₂Cl₂	Trace
4	Pd(dba)₂	Xantphos	CH₂Cl₂	5
5	Pd(acac)₂	Xantphos	CH₂Cl₂	24
6	Pd₂(dba)₃	Xantphos	CH₂Cl₂	68
7	Pd₂(dba)₃	DPPB	CH₂Cl₂	57
8	Pd₂(dba)₃	DPPE	CH₂Cl₂	Trace
9	Pd₂(dba)₃	PPh₃	CH₂Cl₂	Trace
10	Pd₂(dba)₃	DPPF	CH₂Cl₂	46
11	Pd₂(dba)₃	DPEPhos	CH₂Cl₂	35
12	Pd₂(dba)₃	Xantphos	THF	23
13	Pd₂(dba)₃	Xantphos	Toluene	Trace
14	Pd₂(dba)₃	Xantphos	DMF	N.R.
15	Pd₂(dba)₃	Xantphos	CH₃CN	Trace
16^b	Pd₂(dba)₃	Xantphos	CH₂Cl₂	30

Entry	Catalyst	Ligand	Solvent	Yield^c/%
1	PdCl₂	Xantphos	CH₂Cl₂	N.R.
2	Pd(PPh₃)₄	Xantphos	CH₂Cl₂	N.R.
3	Pd(OAc)₂	Xantphos	CH₂Cl₂	Trace
4	Pd(dba)₂	Xantphos	CH₂Cl₂	5
5	Pd(acac)₂	Xantphos	CH₂Cl₂	24
6	Pd₂(dba)₃	Xantphos	CH₂Cl₂	68
7	Pd₂(dba)₃	DPPB	CH₂Cl₂	57
8	Pd₂(dba)₃	DPPE	CH₂Cl₂	Trace
9	Pd₂(dba)₃	PPh₃	CH₂Cl₂	Trace
10	Pd₂(dba)₃	DPPF	CH₂Cl₂	46
11	Pd₂(dba)₃	DPEPhos	CH₂Cl₂	35
12	Pd₂(dba)₃	Xantphos	THF	23
13	Pd₂(dba)₃	Xantphos	Toluene	Trace
14	Pd₂(dba)₃	Xantphos	DMF	N.R.
15	Pd₂(dba)₃	Xantphos	CH₃CN	Trace
16^b	Pd₂(dba)₃	Xantphos	CH₂Cl₂	30

Entry	Catalyst	Ligand	Solvent	Yield^c/%
1	Ni(DPPE)Cl₂	Xantphos	CH₃CN	N.R.
2	Ni(cod)₂	Xantphos	CH₃CN	21
3	Ni(PPh₃)₂Cl₂	Xantphos	CH₃CN	Trace
4	Ni[P(Cy)₃]₂Cl₂	Xantphos	CH₃CN	18
5	NiCl₂	Xantphos	CH₃CN	50
6	NiBr₂	Xantphos	CH₃CN	63
7	NiBr₂	DPPB	CH₃CN	N.D.
8	NiBr₂	DPPE	CH₃CN	N.R.
9	NiBr₂	PPh₃	CH₃CN	N.R.
10	NiBr₂	DPPF	CH₃CN	N.D.
11	NiBr₂	DPEPhos	CH₃CN	35
12	NiBr₂	Xantphos	THF	N.R.
13	NiBr₂	Xantphos	Toluene	N.R.
14	NiBr₂	Xantphos	DMF	N.R.
15^b	NiBr₂	Xantphos	CH₃CN	21

Entry	Catalyst	Ligand	Solvent	Yield^c/%
1	Ni(DPPE)Cl₂	Xantphos	CH₃CN	N.R.
2	Ni(cod)₂	Xantphos	CH₃CN	21
3	Ni(PPh₃)₂Cl₂	Xantphos	CH₃CN	Trace
4	Ni[P(Cy)₃]₂Cl₂	Xantphos	CH₃CN	18
5	NiCl₂	Xantphos	CH₃CN	50
6	NiBr₂	Xantphos	CH₃CN	63
7	NiBr₂	DPPB	CH₃CN	N.D.
8	NiBr₂	DPPE	CH₃CN	N.R.
9	NiBr₂	PPh₃	CH₃CN	N.R.
10	NiBr₂	DPPF	CH₃CN	N.D.
11	NiBr₂	DPEPhos	CH₃CN	35
12	NiBr₂	Xantphos	THF	N.R.
13	NiBr₂	Xantphos	Toluene	N.R.
14	NiBr₂	Xantphos	DMF	N.R.
15^b	NiBr₂	Xantphos	CH₃CN	21

1β-/3R-芳基硫代糖的区域与立体选择性合成

Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar

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