Crystal and molecular structures of the pentaacetates of d-gluconic acid and derived tert-butyl- and tert-butylperoxyesters and the tetra- O-acetyl-1,2- O- tert-butyl-peroxyorthoacetyl derivative

• Published in: Carbohydrate research 1997-12, Vol.305 (2), p.147-154
• Main Authors: Köll, Peter, Bruns, Rainer, Kopf, Jürgen
• Format: Article
• Language: English
• Subjects: 1,3-Parallel interactions; Conformation; d-Gluconic acid esters, protected; d-Gluconic acid, protected; Peroxyesters; X-ray structures
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(97)10019-2

The crystal structures of 2,3,4,5,6- penta-O- acetyl- d-gluconic acid ( 1), 2,3,4,5,6- penta-O- acetyl- d-gluconic acid tert-butylester ( 2), 2,3,4,5,6- penta-O- acetyl- d-gluconic acid tert-butylperoxyester ( 3) and 3,4,5,6- tetra-O- acetyl-1,2-(tert- butylperoxyorthoacetyl)- d-gluconic acid ( 4) were determined by X-ray crystallography, using direct methods, and refined to final conventional residual parameters of R = 0.050, 0.037, 0.042 and 0.042, respectively. In all cases, a planar zigzag conformation of the carbon chain is adopted with a resulting 1,3-parallel interaction between O-2 and O-4. In 2, a second 1,3-parallel alignment between O-3 and the esterified oxygen at C-1 is observed. The peroxycarbonyl group in 3 is essentially planar with a torsion angle about the OO bond of −119° for 3 and 145° for 4.