Chinese Journal of Organic Chemistry >
Pd-Catalyzed Stereoselective Synthesis of Nitroalkyl β-C-Glycosides
Received date: 2023-03-14
Revised date: 2023-05-08
Online published: 2023-05-30
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)
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
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 . DOI: 10.6023/cjoc202303019
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