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Palladium-Catalyzed Directing-Group-Mediated γ-C(sp3)-H Glycosylation for Synthesis of C-Alkyl Glycosides

文献类型：期刊论文

作者Zhong, Qiuyu3,4; Yu, Changyue3; Wang, Jinlin3; Wang, Jiang2; Chen, Kaixian3,4; Liu, Hong1,3,4; Dai, Wenhao1,3
刊名ADVANCED SYNTHESIS & CATALYSIS
出版日期2024-10-15
页码9
关键词C-alkyl glycosides Glycosylation Pd-catalyzed Amino acid gamma-C(sp(3))-H functionalization
ISSN号1615-4150
DOI10.1002/adsc.202400564
通讯作者Liu, Hong(hliu@simm.ac.cn) ; Dai, Wenhao(dwh1992@163.com)
英文摘要C-alkyl glycosides play a crucial role in various bioactive compounds. However, the synthesis of C-alkyl glycosides poses significant challenges, particularly through C(sp(3))-H glycosylation. Here, we report a set of reactions for constructing C-alkyl glycosides through directing-group-mediated functionalization of unactivated gamma-C(sp(3))-H bonds under mild conditions. These reactions not only achieve high regioselectivity and stereoselectivity in glycosylation, but also exhibit a wide substrate scope. They are compatible with both arene and alkane substrates, as well as natural and unnatural amino acid substrates. Mechanistic studies have shown that the directing-group 8-aminoquinoline (AQ) and picolinamide (PA) may affect the chirality of the beta-carbon of L-valine through a sterically favorable trans-palladacycle intermediate, resulting in (R) or (S) configuration of glycosylated amino acid, respectively. These reactions are promising to provide a convenient and powerful tool for constructing C-alkyl glycosides and carbohydrate-based drugs in the future.
WOS关键词N-QUINOLYL BENZAMIDES ; H FUNCTIONALIZATION ; C(SP(3))-H BONDS ; ARYL ; ARYLATION ; INHIBITOR ; PEPTIDES
资助项目National Natural Science Foundation of China[82341091] ; National Natural Science Foundation of China[22107107] ; National Natural Science Foundation of China[82130105] ; National Natural Science Foundation of China[22337003] ; National Natural Science Foundation of China[82121005] ; National Key R&D Program of China[2021YFC0864900] ; China Postdoctoral Science Foundation[BX202133]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001335891900001
出版者WILEY-V C H VERLAG GMBH
源URL[http://119.78.100.183/handle/2S10ELR8/314014]  
专题新药研究国家重点实验室
通讯作者Liu, Hong; Dai, Wenhao
作者单位1.Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310024, Peoples R China
2.Lingang Lab, Shanghai 200031, Peoples R China
3.Univ Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, 555 Zu Chong Zhi Rd, Shanghai 201203, Peoples R China
4.China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Peoples R China
推荐引用方式
GB/T 7714		 Zhong, Qiuyu,Yu, Changyue,Wang, Jinlin,et al. Palladium-Catalyzed Directing-Group-Mediated γ-C(sp3)-H Glycosylation for Synthesis of C-Alkyl Glycosides[J]. ADVANCED SYNTHESIS & CATALYSIS,2024:9.
APA Zhong, Qiuyu.,Yu, Changyue.,Wang, Jinlin.,Wang, Jiang.,Chen, Kaixian.,...&Dai, Wenhao.(2024).Palladium-Catalyzed Directing-Group-Mediated γ-C(sp3)-H Glycosylation for Synthesis of C-Alkyl Glycosides.ADVANCED SYNTHESIS & CATALYSIS,9.
MLA Zhong, Qiuyu,et al."Palladium-Catalyzed Directing-Group-Mediated γ-C(sp3)-H Glycosylation for Synthesis of C-Alkyl Glycosides".ADVANCED SYNTHESIS & CATALYSIS (2024):9.

入库方式： OAI收割

来源：上海药物研究所

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