Synthesis of novel O-acylated-D-ribono-1,5-lactones and structural assignment supported by conventional NOESY-NMR and x-ray analysis

Journal of the Brazilian Chemical Society

Marcus M. Sá²  Gustavo P. Silveira²  Miguel S. B. Caro²  Javier Ellena¹ 

[1] ,Universidade Federal de Santa Catarina Departamento de Química Florianópolis SC ,Brazil

关键词: O-acyl-D-ribono-1;    5-lactones;    D-ribono-1;    4-lactones;    structural elucidation;    sugar lactones;    acylation;   

DOI  :  10.1590/S0103-50532008000100004

来源: SciELO

【 摘 要 】

A practical method for the structural assignment of 3,4-O-benzylidene-D-ribono-1,5-lactones and analogues using conventional NMR techniques and NOESY measurements in solution is described. 2-O-Acyl-3,4-O-benzylidene-D-ribono-1,5-lactones were prepared in good yields by acylation of Zinner’s lactone with acyl chlorides under mildly basic conditions. Structural determination of 2-O-(4-nitrobenzoyl)-3,4-O-benzylidene-D-ribono-1,5-lactone was achieved by single crystal x-ray diffraction, which supports the results based on spectroscopic data.

【 授权许可】

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