ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Partial methanolysis and hydrazinolysis of some derivatives of 1,6-anhydro- ß-_D-glucopyranose

Š. Kučár, I. Tvaroška, J. Zemek, D. Anderle, and M. Matulová

Institute of Chemistry, Centre for Chemical Research, Slovak Academy of Sciences, CS-842 38 Bratislava

Abstract: The effect of polar and steric factors of the substituent attached to carbonyl group of the ester on the course of hydrolysis of per-0-butyryl and per-0-palmitoyl derivatives of l,6-anhydro-ß -_D-glucopyranose has been followed. The stability and electron structure of 1,6-anhydro-ß-_D-glucopyranose as well as of neutral and protonated forms of its acyl derivatives were calculated by the PCILO quantum-chemical method. The experimental data and the results of calculations indicate that different reactivity of acyloxy group at C-3 in dependence on the reaction conditions (in methanolysis the lowest, in hydrazinolysis the highest) is due to the possible stabilization of the activated complex by the 0-3 ...H...0-1 hydrogen bond. The preparation of all 12 mono- and di-O-butyryl and -palmitoyl derivatives of 1,6-anhydro-ß-_D-glucopyranose is described.

Full paper in Portable Document Format: 423a389.pdf

Chemical Papers 42 (3) 389–399 (1988)