Novel aza-C-disaccharide analogues have been conveniently synthesized by using the isoxazoline-linked C-disaccharide derivatives as the intermediates. Firstly, the C=N of isoxazoline was reduced to C-N by using DIBAL-H as reducing agent, then followed by the tandem multi-step reactions through catalytic hydrogenation with Pd(OH)2/C involving debenzylated, reductive cleavage of the N-O, condensation-cyclization of the aldehyde and the in situ generated amine group to form imine C=N and then C=N hydrogenation to form C-N, thus providing a practical and new access to the synthesis of novel aza-C-disaccharide analogues.
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A convenient synthesis of novel aza-C-disaccharide analogues.
Carbohydr Res
October 2014
Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China; Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, Hebei University, Baoding 071002, China. Electronic address:
Novel aza-C-disaccharide analogues have been conveniently synthesized by using the isoxazoline-linked C-disaccharide derivatives as the intermediates. Firstly, the C=N of isoxazoline was reduced to C-N by using DIBAL-H as reducing agent, then followed by the tandem multi-step reactions through catalytic hydrogenation with Pd(OH)2/C involving debenzylated, reductive cleavage of the N-O, condensation-cyclization of the aldehyde and the in situ generated amine group to form imine C=N and then C=N hydrogenation to form C-N, thus providing a practical and new access to the synthesis of novel aza-C-disaccharide analogues.
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