Nucleosides from carbohydrate adducts of diaminomaleonitrile. A novel synthesis of 5-amino-1-(. beta.-D-ribofuranosyl) imidazole-4-carboxamide and 5-amino-1-(. …

JP Ferris, B Devadas, CH Huang…

Index: Ferris, James P.; Devadas, Balekadru; Huang, Chun-Hsien; Ren, Wu-Yen Journal of Organic Chemistry, 1985 , vol. 50, # 6 p. 747 - 754

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Citation Number: 20

Abstract

The stereospecific and regiospecific synthesis of 5-amino-l-(~-~-ribofuranosyl) imidazole-4- carboxamide(16) waa achieved in six steps. A key intermediate in the synthesis, N-(2', 3', 5'- tri-O-benzoyl-(3-~-ribofuranosyl) di-aminomaleonitrile (3), was prepared by two routes: the reaction of diaminomaleonitrile (1) with l-bromo-2, 3, 5-tri-0-benzoyl-p-~-ribofuranose (2) and the reaction of the bis (trimethylsily1) derivative of diaminomaleonitrile (4) with 1-0- ...