Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides

doi:10.6023/cjoc202303019

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3216-3225.DOI: 10.6023/cjoc202303019 Previous Articles Next Articles

钯催化立体选择性合成硝基烷类β-碳糖苷

王兢睿, 冯永奎, 王能中, 黄年玉^*(), 姚辉^*()

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

收稿日期:2023-03-14 修回日期:2023-05-08 发布日期:2023-05-29
作者简介:^† 共同第一作者.
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); 高等学校学科创新引智计划(D20015); 湖北省自然科学基金(2022CFB838); 湖北省教育厅(D20221204); 湖北省教育厅(Q20221212)

Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides

Jingrui Wang, Yongkui Feng, Nengzhong Wang, Nianyu Huang(), Hui Yao()

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:2023-03-14 Revised:2023-05-08 Published:2023-05-29
Contact: * E-mail: huangny@ctgu.edu.cn;yaohui@ctgu.edu.cn
About author:^† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22207063); Programme of Introducing Talents of Discipline to Universities (111 Project); Programme of Introducing Talents of Discipline to Universities(D20015); Hubei Provincial Natural Science Foundation(2022CFB838); Educational Commission of Hubei Province(D20221204); Educational Commission of Hubei Province(Q20221212)

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Abstract

C-Glycosides have attracted more and more attention in the field of medicine and biology due to their excellent physiological activities and stability to hydrolysis/enzymolysis. However, the challenges of stereoselective control are still high during the synthesis process. In this paper, a method for preparing β-C-glycosides with high stereoselectivity through the reaction of 3,4-O-carbonate-D-galactal and nitroalkane with Pd(acac)₂ and 1,4-bis(diphenylphosphino)butane (DPPB) ligand at room temperature has been reported. The structures of the target compounds have been determined by nuclear magnetic resonance spectroscopy (NMR), high-resolution mass spectra (HRMS) and X-ray single crystal diffraction. The method has a wide range of substrates, and has good compatibility for both electron-withdrawing and electron-donating nitroalkanes. Single β-C-glycosides were obtained with high yields, which provide a reliable method for the rapid construction of C-glycoside libraries.

Key words: glycals, stereoselectivity, C-galactosides, C-glycosylation, palladium catalysis

Cite this article

Jingrui Wang, Yongkui Feng, Nengzhong Wang, Nianyu Huang, Hui Yao. Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3216-3225.

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References 19

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Entry	Catalyst	Ligand	Solvent	Yield^b^,^d/%
1	White catalyst	Xantphos	THF	N.R.
2	PdCl₂	Xantphos	THF	N.R.
3	Pd₂(dba)₃	Xantphos	THF	N.R.
4	Pd(PPh₃)₄	Xantphos	THF	N.R.
5	Pd(OAc)₂	Xantphos	THF	10
6	Pd(acac)₂	Xantphos	THF	73
7	Pd(acac)₂	—	THF	N.R.
8	Pd(acac)₂	P(Cy)₃	THF	57
9	Pd(acac)₂	^tBuXphos	THF	66
10	Pd(acac)₂	DPPF	THF	74
11	Pd(acac)₂	DPPB	THF	86
12	Pd(acac)₂	DPPB	Toluene	76
13	Pd(acac)₂	DPPB	CH₃CN	88
14	Pd(acac)₂	DPPB	CH₂Cl₂	95
15^c	Pd(acac)₂	DPPB	CH₂Cl₂	23^c
16	Fe(acac)₃	DPPB	CH₂Cl₂	N.R.
17	Co(acac)₂	DPPB	CH₂Cl₂	N.R.
18	Ni(acac)₂	DPPB	CH₂Cl₂	N.R.
19	Cu(acac)₂	DPPB	CH₂Cl₂	N.R.

Entry	Catalyst	Ligand	Solvent	Yield^b^,^d/%
1	White catalyst	Xantphos	THF	N.R.
2	PdCl₂	Xantphos	THF	N.R.
3	Pd₂(dba)₃	Xantphos	THF	N.R.
4	Pd(PPh₃)₄	Xantphos	THF	N.R.
5	Pd(OAc)₂	Xantphos	THF	10
6	Pd(acac)₂	Xantphos	THF	73
7	Pd(acac)₂	—	THF	N.R.
8	Pd(acac)₂	P(Cy)₃	THF	57
9	Pd(acac)₂	^tBuXphos	THF	66
10	Pd(acac)₂	DPPF	THF	74
11	Pd(acac)₂	DPPB	THF	86
12	Pd(acac)₂	DPPB	Toluene	76
13	Pd(acac)₂	DPPB	CH₃CN	88
14	Pd(acac)₂	DPPB	CH₂Cl₂	95
15^c	Pd(acac)₂	DPPB	CH₂Cl₂	23^c
16	Fe(acac)₃	DPPB	CH₂Cl₂	N.R.
17	Co(acac)₂	DPPB	CH₂Cl₂	N.R.
18	Ni(acac)₂	DPPB	CH₂Cl₂	N.R.
19	Cu(acac)₂	DPPB	CH₂Cl₂	N.R.

钯催化立体选择性合成硝基烷类β-碳糖苷

Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides

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