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Synthese und Eigenschaften von Isopterinnucleosiden ‐ Strukturanaloga des Cytidins. Nucleoside, X [1]
Author(s) -
Harzer Klaus,
Pfleiderer Wolfgang
Publication year - 1973
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19730560407
Subject(s) - chemistry , saponification , alkaline hydrolysis , silylation , nucleophilic substitution , nucleoside , derivative (finance) , hydrolysis , nucleophile , stereochemistry , medicinal chemistry , organic chemistry , catalysis , financial economics , economics
Isopterin ( 1 ), its 6,7‐diphenyl ( 2 ) and 4‐dimethylamino derivative ( 3 ) react after silylation by hexamethyldisilazane with halogenoses 7 and 8 to the blocked isopterin‐N‐1‐nucleosides 9 , 10 , 11 , 20 and 22 , which form the free ribosides 12 , 13 and 14 and 2‐desoxyribosides 21 and 23 on saponification. The easy nucleophilic substitution of the 4‐amino substituents allows the synthesis of further derivatives ( 15 ) as well as formation of lumazine nucleosides ( 17 and 18 ) by alkaline hydrolysis. The structures of the new compounds have been elucidated by UV. and NMR. spectroscopic investigations.