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Steroids ; 152: 108488, 2019 12.
Artigo em Inglês | MEDLINE | ID: mdl-31499076

RESUMO

The regioselective opening of the F ring of 22-oxo-23-spiroketals 7a-d using TiCl4 in acetic anhydride yielded the novel furostanols 11a-d along with cholestanic derivatives 8a-d with pyranone E ring. The structures of the new derivatives thus obtained were established using one- (DEPT) and two-dimensional 1H, 13C NMR experiments (COSY, HSQC, HMBC, NOESY). The 22α-hydroxyl orientation in compounds 11a-d was proposed by comparison of the 13C chemical shifts with those of other aglycone members of this family, and confirmed by combined NOESY and X-ray diffraction analysis of compound 11a.


Assuntos
Furanos/química , Glicosídeos/química , Sapogeninas/síntese química , Compostos de Espiro/química , Esteróis/química , Titânio/química , Catálise , Modelos Moleculares , Conformação Molecular , Sapogeninas/química
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