Synthesis of Racemic 9-(6- and 2,6-Substituted 9H-Purin-9-yl)-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols, Novel Conformationally Locked Carbocyclic Nucleosides

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Title:Synthesis of Racemic 9-(6- and 2,6-Substituted 9H-Purin-9-yl)-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols, Novel Conformationally Locked Carbocyclic Nucleosides
Creators:
Hřebabecký, Hubert
Masojídková, Milena
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 1, pp. 103-123
Uncontrolled Keywords:Oximes, Carbanucleosides, Carbocyclic nucleosides, Purines, Nucleosides, Amines, Norbornanes, LNA, Antivirals

Abstract

(1<i>R</i>*,3<i>R</i>*,6<i>R</i>*,7<i>S</i>*,9<i>S</i>*)- and (1<i>R</i>*,3<i>R</i>*,6<i>R</i>*,7<i>S</i>*,9<i>R</i>*)-9-Amino-5-oxatricyclo[4.2.1.0<sup>3,7</sup>]nonane-3-methanols (<strong>16a</strong> and <strong>17a</strong>) were prepared from 2-(hydroxymethyl)bicyclo[2.2.1]hept-5-ene-2-methanol (<strong>10</strong>) in five easy steps. The amines <strong>16a</strong> and <strong>17a</strong> were used to construct 6-chloro-9<i>H</i>-purine <strong>20</strong> and <strong>21</strong>, 2-amino-6-chloro-9<i>H</i>-purine <strong>30</strong> and <strong>31</strong>, and 6-chloro-8-methyl-9<i>H</i>-purine analogues <strong>34</strong> and <strong>35</strong>. Ammonolysis of these compounds led to 6-amino-9<i>H</i>-purine <strong>22a</strong> and <strong>23a</strong>, 2,6-diamino-9<i>H</i>-purine <strong>32</strong> and <strong>33</strong>, and 6-amino-8-methyl-9<i>H</i>-purine derivatives of 5-oxatricyclo[4.2.1.0<sup>3,7</sup>]nonane-3-methanol <strong>36</strong> and <strong>37</strong>. (1<i>R</i>*,3<i>R</i>*,6<i>R</i>*,7<i>S</i>*,9<i>S</i>*)- and (1<i>R</i>*,3<i>R</i>*,6<i>R</i>*,7<i>S</i>*,9<i>R</i>*)-9-[6-(Dimethylamino)-9<i>H</i>-purin-9-yl]-5-oxatricyclo[4.2.1.0<sup>3,7</sup>]nonane-3-methanols (<strong>22b</strong> and <strong>23b</strong>), and (1<i>R</i>*,3<i>R</i>*,6<i>R</i>*,7<i>S</i>*,9<i>S</i>*)- and (1<i>R</i>*,3<i>R</i>*,6<i>R</i>*,7<i>S</i>*,9<i>R</i>*)-9-[6-(cyclopropylamino)-9<i>H</i>-purin-9-yl]-5-oxatricyclo[4.2.1.0<sup>3,7</sup>]nonane-3-methanols (<strong>22c</strong> and <strong>23c</strong>) were prepared by aminolysis of <strong>20</strong> and <strong>21</strong>. <p>

Title:Synthesis of Racemic 9-(6- and 2,6-Substituted 9H-Purin-9-yl)-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols, Novel Conformationally Locked Carbocyclic Nucleosides
Creators:
Hřebabecký, Hubert
Masojídková, Milena
Holý, Antonín
Uncontrolled Keywords:Oximes, Carbanucleosides, Carbocyclic nucleosides, Purines, Nucleosides, Amines, Norbornanes, LNA, Antivirals
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:70
Number:1
Page Range:pp. 103-123
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20050103UNSPECIFIED
ID Code:2346
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Hřebabecký, Hubert; Masojídková, Milena; Holý, Antonín (2005) Synthesis of Racemic 9-(6- and 2,6-Substituted 9H-Purin-9-yl)-5-oxatricyclo[4.2.1.03,7]nonane-3-methanols, Novel Conformationally Locked Carbocyclic Nucleosides. Collection of Czechoslovak Chemical Communications, 70 (1). pp. 103-123. ISSN 0010-0765

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