Synthesis of Purine Nucleoside Analogues Derived from Carbocyclic 5-C-(Hydroxymethyl)hexopyranoses

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Title:Synthesis of Purine Nucleoside Analogues Derived from Carbocyclic 5-C-(Hydroxymethyl)hexopyranoses
Creators:
Hřebabecký, Hubert
Masojídková, Milena
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 2, pp. 435-452
Uncontrolled Keywords:Guanine, Cyclohexanes, 6-(Cyclopropylamino)purine, Carbocyclic nucleosides, Carbocyclic hexopyranoses, Purines, Nucleosides, Azides, Carbasugars, Adenine

Abstract

(1<i>R</i>,2<i>R</i>,3<i>R</i>,4<i>S</i>)-3-(Benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol (<strong>1</strong>) was converted to (3a<i>S</i>,4<i>R</i>,5<i>S</i>,7a<i>R</i>)-4-(benzyloxy)-2-oxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ<sup>4</sup>-1,3,2-benzodioxathiol-5-ol (<strong>3</strong>) and subsequently to (3a<i>S</i>,4<i>R</i>,5<i>S</i>,7a<i>R</i>)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ<sup>4</sup>-1,3,2-benzodioxathiol-5-yl benzoate (<strong>4</strong>). Treatment of sulfate <strong>4</strong> with adenine and DBU afforded, after deprotection, <strong>7</strong> and <strong>22</strong> in low yields. Reaction of sulfite <strong>3</strong> with lithium azide gave (1<i>R</i>,2<i>R</i>,3<i>S</i>,6<i>S</i>)-6-azido-2-(benzyloxy)-4,4-bis[(trityloxy)methyl]-cyclohexane-1,3-diol (<strong>10</strong>) and (1<i>S</i>,4<i>R</i>,5<i>S</i>,6<i>S</i>)-5-azido-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]-cyclohexane-1,4-diol (<strong>11</strong>) which were, after separation, reduced with LAH to (1<i>R</i>,2<i>R</i>,3<i>S</i>,6<i>S</i>)-6-amino-2-(benzyloxy)-4,4-bis[(trityloxy)methyl]cyclohexane-1,3-diol (<strong>9</strong>) and (1<i>S</i>,4<i>R</i>,5<i>S</i>,6<i>S</i>)-5-amino-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexane-1,4-diol (<strong>12</strong>). Amino derivatives <strong>9</strong> and <strong>12</strong> were transformed to (1<i>R</i>,2<i>R</i>,3<i>S</i>,6<i>S</i>)-6-(6-amino-9<i>H</i>-purin-9-yl)-4,4-bis(hydroxymethyl)cyclohexane-1,2,3-triol (<strong>7</strong>), (1<i>R</i>,2<i>R</i>,3<i>S</i>,6<i>S</i>)-6-[6-(cyclopropylamino)-9<i>H</i>-purin-9-yl]-4,4- bis(hydroxymethyl)cyclohexane-1,2,3-triol (<strong>16</strong>), (1<i>S</i>,2<i>S</i>,3<i>S</i>,4<i>R</i>)-3-[6-(cyclopropylamino)-9<i>H</i>-purin-9-yl]-6,6-bis(hydroxymethyl)cyclohexane-1,2,4-triol (<strong>20</strong>), (1<i>S</i>,2<i>S</i>,3<i>S</i>,4<i>R</i>)-3-(6-amino-9<i>H</i>-purin-9-yl)-6,6-bis(hydroxymethyl)cyclohexane-1,2,4-triol (<strong>22</strong>), and 2-amino-9-[(1<i>S</i>,2<i>R</i>,3<i>R</i>,4<i>S</i>)- 2,3,4-trihydroxy-5,5-bis(hydroxymethyl)cyclohexyl]-9<i>H</i>-purin-6(1<i>H</i>)-one (<strong>27</strong>). <p>

Title:Synthesis of Purine Nucleoside Analogues Derived from Carbocyclic 5-C-(Hydroxymethyl)hexopyranoses
Creators:
Hřebabecký, Hubert
Masojídková, Milena
Holý, Antonín
Uncontrolled Keywords:Guanine, Cyclohexanes, 6-(Cyclopropylamino)purine, Carbocyclic nucleosides, Carbocyclic hexopyranoses, Purines, Nucleosides, Azides, Carbasugars, Adenine
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:69
Number:2
Page Range:pp. 435-452
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20040435UNSPECIFIED
ID Code:2222
Item Type:Article
Deposited On:06 Feb 2009 17:16
Last Modified:06 Feb 2009 16:16

Citation

Hřebabecký, Hubert; Masojídková, Milena; Holý, Antonín (2004) Synthesis of Purine Nucleoside Analogues Derived from Carbocyclic 5-C-(Hydroxymethyl)hexopyranoses. Collection of Czechoslovak Chemical Communications, 69 (2). pp. 435-452. ISSN 0010-0765

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