Stereoselective Synthesis of 2-Deoxythiosugars from Glycals
2-deoxythiosugars are more stable than 2-deoxysugars occurring broadly in bioactive natural products and pharmaceutical agents. An effective and direct methodology to stereoselectively synthesize α-2-deoxythioglycosides catalyzed by AgOTf has been developed. Various alkyl thiols and thiophenols were...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-11-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/22/7979 |
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| author | Xueying You Yifei Cai Chenyu Xiao Lijuan Ma Yong Wei Tianpeng Xie Lei Chen Hui Yao |
| author_facet | Xueying You Yifei Cai Chenyu Xiao Lijuan Ma Yong Wei Tianpeng Xie Lei Chen Hui Yao |
| author_sort | Xueying You |
| collection | DOAJ |
| description | 2-deoxythiosugars are more stable than 2-deoxysugars occurring broadly in bioactive natural products and pharmaceutical agents. An effective and direct methodology to stereoselectively synthesize α-2-deoxythioglycosides catalyzed by AgOTf has been developed. Various alkyl thiols and thiophenols were explored and the desired products were formed in good yields with excellent α-selectivity. This method was further applied to the syntheses of <i>S</i>-linked disaccharides and late-stage 2-deoxyglycosylation of estrogen, L-menthol, and zingerone thiols successfully. |
| first_indexed | 2024-03-09T18:07:20Z |
| format | Article |
| id | doaj.art-c6fe7fe85b764a3994674cd558049fae |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T18:07:20Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-c6fe7fe85b764a3994674cd558049fae2023-11-24T09:24:22ZengMDPI AGMolecules1420-30492022-11-012722797910.3390/molecules27227979Stereoselective Synthesis of 2-Deoxythiosugars from GlycalsXueying You0Yifei Cai1Chenyu Xiao2Lijuan Ma3Yong Wei4Tianpeng Xie5Lei Chen6Hui Yao7Hubei 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, ChinaHubei 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, ChinaHubei 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, ChinaHubei 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, ChinaYichang Humanwell Pharmaceutical Co., Ltd., Yichang 443000, ChinaYichang Humanwell Pharmaceutical Co., Ltd., Yichang 443000, ChinaYichang Humanwell Pharmaceutical Co., Ltd., Yichang 443000, ChinaHubei 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, China2-deoxythiosugars are more stable than 2-deoxysugars occurring broadly in bioactive natural products and pharmaceutical agents. An effective and direct methodology to stereoselectively synthesize α-2-deoxythioglycosides catalyzed by AgOTf has been developed. Various alkyl thiols and thiophenols were explored and the desired products were formed in good yields with excellent α-selectivity. This method was further applied to the syntheses of <i>S</i>-linked disaccharides and late-stage 2-deoxyglycosylation of estrogen, L-menthol, and zingerone thiols successfully.https://www.mdpi.com/1420-3049/27/22/79792-deoxythioglycosidesglycosylationsilver triflatestereoselective synthesisglycals |
| spellingShingle | Xueying You Yifei Cai Chenyu Xiao Lijuan Ma Yong Wei Tianpeng Xie Lei Chen Hui Yao Stereoselective Synthesis of 2-Deoxythiosugars from Glycals Molecules 2-deoxythioglycosides glycosylation silver triflate stereoselective synthesis glycals |
| title | Stereoselective Synthesis of 2-Deoxythiosugars from Glycals |
| title_full | Stereoselective Synthesis of 2-Deoxythiosugars from Glycals |
| title_fullStr | Stereoselective Synthesis of 2-Deoxythiosugars from Glycals |
| title_full_unstemmed | Stereoselective Synthesis of 2-Deoxythiosugars from Glycals |
| title_short | Stereoselective Synthesis of 2-Deoxythiosugars from Glycals |
| title_sort | stereoselective synthesis of 2 deoxythiosugars from glycals |
| topic | 2-deoxythioglycosides glycosylation silver triflate stereoselective synthesis glycals |
| url | https://www.mdpi.com/1420-3049/27/22/7979 |
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