Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols

Synthesis of 10-membered bislactones by PCC oxidation of methyl 2,6-di-O-pivaloyl-α-D-glucopyranoside and methyl 4,6-O-benzylidene-α-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.

Keywords

sugar bislactones keto sugars pyridinium chlorochromate regioselective oxidation bioactivity studies

URI

http://hdl.handle.net/10400.15/4548

Citation

Rauter, A.P.; Piedade, F.; Almeida, T.; Ramalho, R.; Ferreira, M.J.; Resende, R.; Amado, J.; Pereira, H.; Justino, J.; Neves, A.; Silva, F.V.M. & Canda, T. (2004). Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols. Carbohydrate Research, 339(11), 1889-1897. DOI:10.1016/j.carres.2004.06.002