Studies on the Syntheses of Compounds related to Adenosine 3', 5'-cyclic Phosphate. II. Removal of Etheno Group of 2-Substituted 1, N⁶-Etheno-adenosine 3', 5'-cyclic Phosphates

Abstract

Treatment of 2-substituted 1, N⁶-etheno-c-AMP (c-AMP : adenosine 3', 5'-cyclic phosphate) derivatives with N-bromosuccinimide (NBS) under mild conditions gave the corresponding 2-substituted-c-AMP. Therefore, the route (c-AMP→1, N⁶-etheno-c-AMP→2-substituted 1, N⁶-etheno-c-AMP→2-substituted c-AMP) offers an excellent way to synthesize the last compound from c-AMP. The yields of this deblocking reaction of the etheno group were increased by the adjustment of the solution to alkaline after bromination. The probable reaction mechanism involving the bromination and the subsequent hydrolysis has been proposed.