Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purin-8(9H)-one

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Title:Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purin-8(9H)-one
Creators:
Janeba, Zlatko
Holý, Antonín
Masojídková, Milena
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 7, pp. 1126-1144
Uncontrolled Keywords:Purines, Alkylation, Nucleosides, Bromination, Phosphonates, Acyclic analogs, Anhydro derivatives, Nucleotides

Abstract

Reaction of 8-bromoadenine derivatives <strong>2</strong> with sodium acetate in acetic acid and cleavage of (<i>S</i>)-7-[(trityloxy)methyl]-7,8-dihydro[1,3]oxazolo[3,2-<i>e</i>]purin-4-amine (<strong>12</strong>) and diisopropyl (<i>S</i>)-{[(4-amino-8,9-dihydro-7<i>H</i>-[1,3]oxazino[3,2-<i>e</i>]purin-8-yl)oxy]methyl}phosphonate (<strong>13a</strong>) were used for the synthesis of the corresponding N<sup>9</sup>-substituted derivatives of 6-amino- 7<i>H</i>-purin-8(9<i>H</i>)-one <strong>3a</strong>-<strong>3c</strong> and <strong>7</strong>. Alkylation of 6-amino-7<i>H</i>-purin-8(9<i>H</i>)-one (<strong>3a</strong>) with diverse alkylation agents afforded the title N<sup>9</sup>-monosubstituted <strong>3b</strong>, <strong>3d</strong> and <strong>7a</strong> and N<sup>7</sup>,N<sup>9</sup>-disub- stituted acyclic nucleoside and nucleotide analogs <strong>6b</strong>, <strong>6d</strong> and <strong>8a</strong>. <p>

Title:Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purin-8(9H)-one
Creators:
Janeba, Zlatko
Holý, Antonín
Masojídková, Milena
Uncontrolled Keywords:Purines, Alkylation, Nucleosides, Bromination, Phosphonates, Acyclic analogs, Anhydro derivatives, Nucleotides
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:7
Page Range:pp. 1126-1144
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20001126UNSPECIFIED
ID Code:1705
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:12

Citation

Janeba, Zlatko; Holý, Antonín; Masojídková, Milena (2000) Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purin-8(9H)-one. Collection of Czechoslovak Chemical Communications, 65 (7). pp. 1126-1144. ISSN 0010-0765

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