The approach to the synthesis of novel amino-C-glycosides

Li Zhiwei, Li Xiaoliu, Duan Kefang, Chen Hua

PDF(367 KB)
PDF(367 KB)
Front. Chem. China ›› 2006, Vol. 1 ›› Issue (3) : 281-286. DOI: 10.1007/s11458-006-0040-y

The approach to the synthesis of novel amino-C-glycosides

  • Li Zhiwei, Li Xiaoliu, Duan Kefang, Chen Hua
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Abstract

Stereoselective 1,3-dipolar cycloadditions of exo-glycals 1 to nitrones 2, 5 and 8 were investigated under the catalysis of Lewis acid or in a refluxing benzene or toluene solution, and afforded the corresponding cycloadducts of ketosyl spiro-isoxazolidines. The reductive cleavage of the N-O bond in the isoxazolidine ring and debenzylation by the catalytic hydrogenation [Pd(OH)2/C] were approached using the glucose-type cycloadducts 6b and 6e to alkyl-C-glycoside derivatives 12, providing a new access to a novel alkyl-C-glycoside containing an amino group on the side alkyl chain.

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Li Zhiwei, Li Xiaoliu, Duan Kefang, Chen Hua. The approach to the synthesis of novel amino-C-glycosides. Front. Chem. China, 2006, 1(3): 281‒286 https://doi.org/10.1007/s11458-006-0040-y
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