CRYSTAL AND MOLECULAR-STRUCTURES OF THE PENTAACETATES OF D-GLUCONIC ACID AND DERIVED TERT-BUTYLPEROXYESTERS AND TERT-BUTYLPEROXYESTERS AND THE TETRA-O-ACETYL-1,2-O-TERT-BUTYL-PEROXYORTHOACETYL DERIVATIVE

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 tertbutylperoxyester (3) and etra-O -acetyl-1,2-(tert-butylperoxyorthoacetyl)-D- gluconic acid (4) were de termined by X-ray crystallography, using direct methods, and refined t o final conventional residual parameters of R = 0.050, 0.037, 0.042 an d 0.042, respectively. In all cases, a planar zigzag conformation of t he carbon chain is adopted with a resulting 1,3-parallel interaction b etween 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 degrees for 3 and 145 degrees for 4. (C) 1998 Elsevier Science L td.