C-glycosides have been demonstrated to have distinct biological functions and therefore display notable pharmacological values,whereas the access to the versatile structural analog of C-glycosides is a significant cha...C-glycosides have been demonstrated to have distinct biological functions and therefore display notable pharmacological values,whereas the access to the versatile structural analog of C-glycosides is a significant challenge to their advancement as therapeutic agents.We herein disclose a facial and efficient catalytic C-glycosylation using a glycosyl ortho-2,2-dimethoxycarbony lcyclopropylbenzoate(CCBz)as the donor.The trailblazing glycosyl donor can be simply activated by a non-toxic and easily accessible Sc(Ⅲ)catalyst.The ring-strain release of the incorporated donor-acceptor cyclopropane(DAC)serves as a powerful driving force of the glycosylation system.The adaptability of current methods to different types of donors and acceptors was exemplified.Examinations on the synthetic potential were done with the one-pot synthesis of free C-indolyl-glycosides and the subsequent biological studies,unlocking the antibacterial potentials of these compounds.展开更多
The Hantzsch synthesis has been used for the preparation of the 1,4-Dihydropyridines compounds with different pharmacophore groups. The use of a designed glycosylated compound in Hantzsch synthesis would lead to a nov...The Hantzsch synthesis has been used for the preparation of the 1,4-Dihydropyridines compounds with different pharmacophore groups. The use of a designed glycosylated compound in Hantzsch synthesis would lead to a novel Dihydropyridines C-Glycosylated compound. We used the 6-methoxy-2, 2-dimethyltetrahydrofuro [3, 4-d] [1, 3] dioxole-4-carbaldehyde as a glycosylated-based aldehydes. The 4-(3,4-Dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxy-lic acid 3-ethyl ester 5-methyl ester was synthesized. The structure of compounds was determined by NMR spectroscopy, FTIR and mass spectroscopy methods. We synthesized this 1,4-Dihydropyridines compound by ionic liquid under ultrasound irradiation as a green chemistry synthesis.展开更多
基金Ministry of Education(MOE-T2EP30120-0007,Tier-1 RG107/23)of Singapore for the financial support.
文摘C-glycosides have been demonstrated to have distinct biological functions and therefore display notable pharmacological values,whereas the access to the versatile structural analog of C-glycosides is a significant challenge to their advancement as therapeutic agents.We herein disclose a facial and efficient catalytic C-glycosylation using a glycosyl ortho-2,2-dimethoxycarbony lcyclopropylbenzoate(CCBz)as the donor.The trailblazing glycosyl donor can be simply activated by a non-toxic and easily accessible Sc(Ⅲ)catalyst.The ring-strain release of the incorporated donor-acceptor cyclopropane(DAC)serves as a powerful driving force of the glycosylation system.The adaptability of current methods to different types of donors and acceptors was exemplified.Examinations on the synthetic potential were done with the one-pot synthesis of free C-indolyl-glycosides and the subsequent biological studies,unlocking the antibacterial potentials of these compounds.
文摘The Hantzsch synthesis has been used for the preparation of the 1,4-Dihydropyridines compounds with different pharmacophore groups. The use of a designed glycosylated compound in Hantzsch synthesis would lead to a novel Dihydropyridines C-Glycosylated compound. We used the 6-methoxy-2, 2-dimethyltetrahydrofuro [3, 4-d] [1, 3] dioxole-4-carbaldehyde as a glycosylated-based aldehydes. The 4-(3,4-Dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxy-lic acid 3-ethyl ester 5-methyl ester was synthesized. The structure of compounds was determined by NMR spectroscopy, FTIR and mass spectroscopy methods. We synthesized this 1,4-Dihydropyridines compound by ionic liquid under ultrasound irradiation as a green chemistry synthesis.
