Convenient Cobalt-Catalyzed Stereoselective Synthesis of β-D-Thioglucosides

doi:10.6023/cjoc202202021

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (7): 2140-2154.DOI: 10.6023/cjoc202202021 Previous Articles Next Articles

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廉价钴催化下β-D-葡萄烯糖硫苷的立体选择性合成

华敏, 孙阳星, 张雪晴, 姚辉^*(), 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湖北宜昌 443002

收稿日期:2022-02-18 修回日期:2022-03-23 发布日期:2022-08-09
通讯作者: 姚辉, 黄年玉
基金资助:
国家自然科学基金(82003621); 湖北省自然科学基金(2020CFB205); 湖北省教育厅自然科学基金(Q20201204)

Convenient Cobalt-Catalyzed Stereoselective Synthesis of β-D-Thioglucosides

Min Hua, Yangxing Sun, Xueqing Zhang, Hui Yao(), Nianyu Huang()

Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang, Hubei 443002

Received:2022-02-18 Revised:2022-03-23 Published:2022-08-09
Contact: Hui Yao, Nianyu Huang
Supported by:
National Natural Science Foundation of China(82003621); Natural Science Foundation of Hubei Province(2020CFB205); Natural Science Foundation of the Educational Commission of Hubei Province(Q20201204)

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Abstract

A method of stereoselective synthesis of β-D-thioglycosides from glucosyl-3-pyridinate donor and thiophenols/ thiols catalyzed by Co(BF₄)₂ was reported. The chemical structures of the target compounds were confirmed by nuclear magnetic resonance, high-resolution mass spectrometry and single crystal X-ray diffraction. The reaction has good functional group compatibility with all kinds of mercaptans and thiophenols, and can tolerate active sulfur nucleophiles including ester group, phenol/alcohol hydroxyl group, amino group and acetylamino group. It can also be used for the efficient synthesis of thioglycopeptides, which provides a new way for the rapid preparation of thioglycosides.

Key words: Co-catalysis, glycosylation reaction, thioglycoside, glycopeptide, synthesis

Cite this article

Min Hua, Yangxing Sun, Xueqing Zhang, Hui Yao, Nianyu Huang. Convenient Cobalt-Catalyzed Stereoselective Synthesis of β-D-Thioglucosides[J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2140-2154.

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References 14

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Entry^a	Donor	T/℃	Yield^b/%	β∶α^c
1	1a	120^d	—	—
2	1b	80	55	8∶1
3	1c	80	50	6∶1
4	1d	80	40	3∶1
5	1e	80	57	7∶1
6	1f	80	40	4∶1

Entry^a	Donor	T/℃	Yield^b/%	β∶α^c
1	1a	120^d	—	—
2	1b	80	55	8∶1
3	1c	80	50	6∶1
4	1d	80	40	3∶1
5	1e	80	57	7∶1
6	1f	80	40	4∶1

Entry^a	[Co]	L	Solvent	T/℃	Yield^b/%	β∶α^c
1	Co(acac)₃	CataCXium A	CH₃CN	60	25	7∶1
2	Co(acac)₃	CataCXium A	CH₃CN	100	59	5∶1
3	CoBr₂	CataCXium A	CH₃CN	80	20	1∶3
4	CoCl₂	CataCXium A	CH₃CN	80	32	1∶2
5	Co(PPh₃)₂Cl₂	CataCXium A	CH₃CN	80	35	4∶1
6	Co(acac)₂	CataCXium A	CH₃CN	80	50	6∶1
7	Co(BF₄)₂	CataCXium A	CH₃CN	80	65	8∶1
8	Co(BF₄)₂	Xantphos	CH₃CN	80	45	1∶1
9	Co(BF₄)₂	DPPE	CH₃CN	80	66	6∶1
10	Co(BF₄)₂	(R)-(–)-DTBM-SEGPHOS	CH₃CN	80	53	7∶1
Entry^a	[Co]	L	Solvent	T/℃	Yield^b/%	β∶α^c
11	Co(BF₄)₂	Ph₃P	CH₃CN	80	40	4∶1
12	Co(BF₄)₂	(S,S)-Chiraphos	CH₃CN	80	60	8∶1
13	Co(BF₄)₂	DPPF	CH₃CN	80	71%	7:1
14	Co(BF₄)₂	(R)-(+)-BINAP	CH₃CN	80	80%	10:1
15	Co(BF₄)₂	(S)-(–)-BINAP	CH₃CN	80	50%	2:1
16	Co(BF₄)₂	(R)-(+)-BINAP	DMF	80	-	-
17	Co(BF₄)₂	(R)-(+)-BINAP	THF	80	47%	5:1

Entry^a	[Co]	L	Solvent	T/℃	Yield^b/%	β∶α^c
1	Co(acac)₃	CataCXium A	CH₃CN	60	25	7∶1
2	Co(acac)₃	CataCXium A	CH₃CN	100	59	5∶1
3	CoBr₂	CataCXium A	CH₃CN	80	20	1∶3
4	CoCl₂	CataCXium A	CH₃CN	80	32	1∶2
5	Co(PPh₃)₂Cl₂	CataCXium A	CH₃CN	80	35	4∶1
6	Co(acac)₂	CataCXium A	CH₃CN	80	50	6∶1
7	Co(BF₄)₂	CataCXium A	CH₃CN	80	65	8∶1
8	Co(BF₄)₂	Xantphos	CH₃CN	80	45	1∶1
9	Co(BF₄)₂	DPPE	CH₃CN	80	66	6∶1
10	Co(BF₄)₂	(R)-(–)-DTBM-SEGPHOS	CH₃CN	80	53	7∶1
Entry^a	[Co]	L	Solvent	T/℃	Yield^b/%	β∶α^c
11	Co(BF₄)₂	Ph₃P	CH₃CN	80	40	4∶1
12	Co(BF₄)₂	(S,S)-Chiraphos	CH₃CN	80	60	8∶1
13	Co(BF₄)₂	DPPF	CH₃CN	80	71%	7:1
14	Co(BF₄)₂	(R)-(+)-BINAP	CH₃CN	80	80%	10:1
15	Co(BF₄)₂	(S)-(–)-BINAP	CH₃CN	80	50%	2:1
16	Co(BF₄)₂	(R)-(+)-BINAP	DMF	80	-	-
17	Co(BF₄)₂	(R)-(+)-BINAP	THF	80	47%	5:1

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廉价钴催化下β-D-葡萄烯糖硫苷的立体选择性合成

Convenient Cobalt-Catalyzed Stereoselective Synthesis of β-D-Thioglucosides

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