Paper
Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purin-8(9H)-one
Published 2000 · Z. Janeba, A. Holý, M. Masojídková
Collection of Czechoslovak Chemical Communications
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Abstract
Reaction of 8-bromoadenine derivatives 2 with sodium acetate in acetic acid and cleavage of ( S )-7-[(trityloxy)methyl]-7,8-dihydro[1,3]oxazolo[3,2- e ]purin-4-amine ( 12 ) and diisopropyl ( S )-{[(4-amino-8,9-dihydro-7 H -[1,3]oxazino[3,2- e ]purin-8-yl)oxy]methyl}phosphonate ( 13a ) were used for the synthesis of the corresponding N 9 -substituted derivatives of 6-amino- 7 H -purin-8(9 H )-one 3a - 3c and 7 . Alkylation of 6-amino-7 H -purin-8(9 H )-one ( 3a ) with diverse alkylation agents afforded the title N 9 -monosubstituted 3b , 3d and 7a and N 7 ,N 9 -disub- stituted acyclic nucleoside and nucleotide analogs 6b , 6d and 8a .
This study demonstrates the synthesis of acyclic nucleoside and nucleotide analogs from 6-amino-7H-purin-8(9H)-one, which can be used as a starting point for the synthesis of nucleoside and nucleotide derivatives.
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