Pentaric acids and derivatives from nitric acid–oxidized pentoses
Pentaric acids and derivatives from nitric acid–oxidized pentoses
Abstract
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.
Type
Journal Article
Type of thesis
Series
Citation
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.
Date
2013
Publisher
Taylor & Francis