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Communication | Special issue | Vol 7, No. 1, 1977, pp.179-192
Published online, 1st January, 1970
DOI: 10.3987/S-1977-01-0179
Synthesis of 1-(5’-Deoxy-β-D-erythropent-4’-enofuranosyl)isocytosine and 2-N,5‘-Anhydroisocytidine

Vinko Skaric,* Jasenka Matulic-Adamic, and Djurdja Skaric

*Laboratory fo Stereochemistry and Natural Products, "Ruder Boskovic" Institute, Bijenicka 54, P.O. Box 1016 41001 Zagreb, Croatia

Abstract

The synthesis of 2-N-benzoyl-1-(2’,3’-O-isopropylidene-5’-deoxy-β-D-erythropent-4’-enofuranosyl)isocytosine (VII) and its conversion into 5’-deoxy-α-L-lyxopentofuranosyl- (XVI) and 2-N,4’-anhydro-1-( 5’-deoxy-5’-bromo-α-L-lyxopentofuranosyl)isocytosine (XVIII), is described. Treatment of 5’-deoxy-5’-iodo- (X) or 5’-O-p-toluenesulphonyl-isocytidine (IV) with potassium phthalimide in dioxan has afforded 2’,3’-O-isopropylidene-2-N-benzoyl-2-N,5’-anhydroisocytidine (VI) in high yields.