Hinton, M. R., Manle-Harris, M., Hardcastle, K. I. & Kiely, D. E. (2013). Pentaric acids and derivatives from nitric acid–oxidized pentoses. Journal of Carbohydrate Chemisty, 32(1), 68-85.
Permanent Research Commons link: http://hdl.handle.net/10289/7870
This report describes the preparation of the four stereoisomeric pentaric acids by nitric acid oxidation of d-xylose, d-arabinose, l-arabinose, and d-ribose, with xylaric, d-arabinaric, and l-arabinaric acids being made in a reactor under computer control. The pentaric acids were converted to their crystalline N,N′-dimethylpentaramides, derivatives that proved useful for isolation of the arabinaric acids from their respective oxidation mixtures. The N,N′-dimethylpentaramides were readily convertible to the corresponding pentaric acid disodium salts in aqueous sodium chloride. The 2,3,4-O-triacetyl-N,N′-dimethylpentaramides of xylaric, l-arabinaric, and ribaric acid were also prepared. Ribaric acid was isolated as crystalline 1,4(5,2)-ribarolactone and further characterized by x-ray crystallography.
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