Synthesis of Carba Analogues of 2'-Deoxy-4'-C-(hydroxymethyl)nucleosides

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Title:Synthesis of Carba Analogues of 2'-Deoxy-4'-C-(hydroxymethyl)nucleosides
Creators:
Hřebabecký, Hubert
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 9, pp. 1485-1496
Uncontrolled Keywords:4'-<i>C</i>-Branched nucleosides, Nucleosides, Cyclopentanes, Additions, Carbanucleosides, Reductions, Carbocyclic nucleosides

Abstract

Racemic dimethyl 2-hydroxy-4-[5-methyl-2(1<i>H</i>),4(3<i>H</i>)-dioxopyrimidin-1-yl]- (<strong>7a</strong> and <strong>8a</strong>) and dimethyl 4-(6-aminopurin-9-yl)-2-hydroxycyclopentane-1,1-dicarboxylates (<strong>7b</strong> and <strong>8b</strong>) were prepared by addition of sodium salt of thymine and adenine, respectively, to dimethyl (<i>Z</i>)-(4-oxobut-2-en-1-yl)malonate (<strong>1</strong>). Reduction of the diesters with sodium borohydride in methanol in the presence of sulfuric acid gave corresponding racemic 2,2-bis(hydroxymethyl)-4-[5-methyl-2(1<i>H</i>),4(3<i>H</i>)-dioxopyrimidin-1-yl]- (<strong>14a</strong> and <strong>15a</strong>), 4-(6-aminopurin- 9-yl)-2,2-bis(hydroxymethyl)cyclopentan-1-ol (<strong>14b</strong> and <strong>15b</strong>), methyl (±)-<i>cis</i>-2-hydroxy- 1-hydroxymethyl-4-[5-methyl-2(1<i>H</i>),4(3<i>H</i>)-dioxopyrimidin-1-yl]- (<strong>13a</strong>), and methyl (±)-<i>cis</i>-4-(6-aminopurin-9-yl)-2-hydroxy-1-hydroxymethylcyclopentan-1-carboxylate (<strong>13b</strong>), respectively. <p>

Title:Synthesis of Carba Analogues of 2'-Deoxy-4'-C-(hydroxymethyl)nucleosides
Creators:
Hřebabecký, Hubert
Holý, Antonín
Uncontrolled Keywords:4'-<i>C</i>-Branched nucleosides, Nucleosides, Cyclopentanes, Additions, Carbanucleosides, Reductions, Carbocyclic nucleosides
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:64
Number:9
Page Range:pp. 1485-1496
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19991485UNSPECIFIED
ID Code:1573
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:10

Citation

Hřebabecký, Hubert; Holý, Antonín (1999) Synthesis of Carba Analogues of 2'-Deoxy-4'-C-(hydroxymethyl)nucleosides. Collection of Czechoslovak Chemical Communications, 64 (9). pp. 1485-1496. ISSN 0010-0765

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