Scalable synthesis of 8-iodo-1-naphthoate via photoinduced Suárez halodecarboxylation for the preparation of glycosyl donors
文献类型：期刊论文
| 作者 | Chen, Mei3,4; Hao, Bangxing2,3; Yang, Liran3,4; Xie, Feiyan2,3; Wang, Panpan2,3; Xu, Peifan2,3; Wei, Jingyang3; Xu, Jimin1; Zhu, Yugen3,4 |
| 刊名 | JOURNAL OF CARBOHYDRATE CHEMISTRY
 |
| 出版日期 | 2025-08-29 |
| 页码 | 29 |
| 关键词 | Glycosyl donor glycosyl naphthoate halodecarboxylation 8-iodo-1-naphthoic acid |
| ISSN号 | 0732-8303 |
| DOI | 10.1080/07328303.2025.2552365 |
| 通讯作者 | Xu, Jimin(xujm37@mail.sysu.edu.cn) ; Zhu, Yugen(zhuyg86@163.com) |
| 英文摘要 | 8-Iodo-1-naphthoate is a key intermediate for the versatile preparation of 1,8-difunctionalized naphthalene derivatives, particularly the glycosyl 8-alkynyl-1-naphthoate donors. Herein, we report an efficient and scalable approach for the synthesis of a variety of 8-iodo-1-naphthoates via a modified photoinduced Su & aacute;rez halodecarboxylation reaction. Derivatization of the 8-iodo-naphthoates enables access to a wide range of 1,8-difunctionalized naphthalene derivatives. In particular, Sonogashira coupling reactions using diverse alkynes clearly demonstrate the superior reactivity and functional group tolerance of 8-iodo-1-naphthoate compared to its bromide counterpart. This practical and cost-effective synthetic approach is expected to greatly facilitate the broader application of glycosyl 8-alkynyl-1-naphthoates in glycosylation chemistry. |
| WOS关键词 | OLIGOSACCHARIDE SYNTHESIS ; IODOSOBENZENE DIACETATE ; SONOGASHIRA REACTION ; EFFICIENT ; CATALYSIS ; ALKYNYLBENZOATES ; PLATFORM ; REAGENT |
| 资助项目 | National Natural Science Foundation of China[22007080] ; Zhongshan Science and Technology Bureau[CXTD2022012] ; Zhongshan Science and Technology Bureau[2019B090904008] ; High-Level Innovative Research Institute[2021B0909050003] ; Department of Science and Technology of Guangdong Province |
| WOS研究方向 | Biochemistry & Molecular Biology ; Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:001560332500001 |
| 出版者 | TAYLOR & FRANCIS INC |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/321357]  |
| 专题 | 中国科学院上海药物研究所 |
| 通讯作者 | Xu, Jimin; Zhu, Yugen |
| 作者单位 | 1.Sun Yat Sen Univ, Sch Publ Hlth Shenzhen, Shenzhen Campus, Shenzhen 518107, Peoples R China 2.Zunyi Med Univ, Zhuhai Campus, Zhuhai 519040, Peoples R China 3.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China 4.Guangzhou Univ Chinese Med, Sch Pharmaceut Sci, Guangzhou 510006, Peoples R China |
| 推荐引用方式 GB/T 7714 | Chen, Mei,Hao, Bangxing,Yang, Liran,et al. Scalable synthesis of 8-iodo-1-naphthoate via photoinduced Suárez halodecarboxylation for the preparation of glycosyl donors[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY,2025:29. |
| APA | Chen, Mei.,Hao, Bangxing.,Yang, Liran.,Xie, Feiyan.,Wang, Panpan.,...&Zhu, Yugen.(2025).Scalable synthesis of 8-iodo-1-naphthoate via photoinduced Suárez halodecarboxylation for the preparation of glycosyl donors.JOURNAL OF CARBOHYDRATE CHEMISTRY,29. |
| MLA | Chen, Mei,et al."Scalable synthesis of 8-iodo-1-naphthoate via photoinduced Suárez halodecarboxylation for the preparation of glycosyl donors".JOURNAL OF CARBOHYDRATE CHEMISTRY (2025):29. |
入库方式： OAI收割
来源：上海药物研究所
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