NUCLEOSIDE SYNTHESIS: A SYSTEMATIC STUDY OF THE INFLUENCE OF THE NATURE AND STEREOCHEMISTRY OF D-ALDOPENTOFURANOSES, AND THE EFFECT OF THE SUBSTITUENT AT C-2, IN THE ACID-CATALYZED FUSION-REACTION WITH INDAZOLE

Article abstract of DOI:10.1016/0008-6215(80)90009-9

A systematic study of the acid-catalyzed fusion-reaction is reported.The influence of the nature and stereochemistry of the D-aldopentofuranose and the effect of the substituent at C-2 have been investigated by using indazole as a model heterocycle.The results obtained show that the nature and stereochemistry of the staring, per-O-acetylated D-aldopentofuranose have no significant effect upon the product distribution of the acid-catalyzed fusion-reaction.The use of a sugar lacking a participating group at C-2 showed, however, that the absence of participation increases the ratio of cis-1',2'-nucleosides, and the mechanism involved is discussed.In all cases, the results indicated that the distribution of the products is determined by their relative, thermodynamic stabilities.