N. B. Khripach, I. Mikhailopulo, A. A. Akhrem
Jun 15, 1982
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Journal
Chemistry of Heterocyclic Compounds
Abstract
The glycosylation of silyl derivatives of N4-benzoylcytosine and N6-benzoyladenine with D-xylal and L-arabinal diacetates in the presence of SnCl4 as the condensing agent was studied. It is shown that the character of the products depends on the heterocyclic base subjected to the condensation. Primarily N1-nucleosides with a double bond in the 2′ position, in which the heterocyclic base is attached to the C1 atom of the carbohydrate fragmnet, are formed with N4-benzoylcytosine, whereas only N9-nucleosides in which the C3 atom of the carbohydrate fragment is bonded to the heterocyclic base are obtained with N6-benzoyladenine under the investigated conditions. The catalytic hydrogenation of the double bond in the carbohydrate fragment of the nucleosides obtained was investigated. The structures of all of the compounds obtained were proved by means of PMR and circular dichroism (CD) spectroscopy.