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Updated: Aug 23, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation
Amélia P Rauter1, Fátima Piedade, Tânia Almeida
1Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Ed. C8, 5 degrees Piso, Campo Grande, 1749-016 Lisboa, Portugal. aprauter@fc.ul.pt
Abstract:
Synthesis of 10-membered bislactones by PCC oxidation of methyl 2,6-di-O-pivaloyl-alpha-D-glucopyranoside and methyl 4,6-O-benzylidene-alpha-D-glucopyranoside is described, with emphasis on their structure elucidation using the information gained by combination of NMR spectroscopic techniques with X-ray diffraction data. In alternative, the use of PCC and PCC adsorbed on silica gel or alumina for the regioselective oxidation of vicinal diols in sugars is also reported. Both bislactones showed antifungal activity against Candida albicans, and were slightly active against the bacteria Bacillus subtilis. The bislactone presenting pivaloyl protecting groups also promoted some growth inhibition of Staphylococcus aureus.
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