Carbocyclic Phosphonate-Based Nucleotide Analogs Related to PMEA II. Racemic cis-Configured Derivatives

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Title:Carbocyclic Phosphonate-Based Nucleotide Analogs Related to PMEA II. Racemic cis-Configured Derivatives
Creators:
Liboska, Radek
Masojídková, Milena
Rosenberg, Ivan
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 5, pp. 778-790
Uncontrolled Keywords:Carbocyclic analogs, Antivirals, Nucleoside phosphonates

Abstract

Racemic <i>N</i>-(<i>cis</i>-2-phosphonomethoxycycloalkyl) derivatives of heterocyclic bases, a novel type of nucleotide analogs related to 9-(2-phosphonomethoxyethyl)adenine (PMEA), are reported. The synthesis of adenine- (<strong>6a</strong>, <strong>6b</strong>), uracil- (<strong>6c</strong>) and cytosine- (<strong>6d</strong>) containing carbocyclic phosphonates is based on the reaction of <i>cis</i>-2-hydroxycycloalkyl derivatives of protected nucleobases with diisopropyl tosyloxymethanephosphonate. The starting purine-containing nucleoside analogs <strong>5a-5f</strong> were prepared by the Mitsunobu reaction of protected nucleobases with <i>trans</i>-2-benzyloxycycloalkanols, whereas pyrimidine-containing nucleoside analogs <strong>5g-5k</strong> were obtained by configurational inversion at C-2' of the corresponding 1-(<i>trans</i>-2-hydroxycycloalkyl)pyrimidines via ring opening of their 2,2'-anhydro derivatives.

Title:Carbocyclic Phosphonate-Based Nucleotide Analogs Related to PMEA II. Racemic cis-Configured Derivatives
Creators:
Liboska, Radek
Masojídková, Milena
Rosenberg, Ivan
Uncontrolled Keywords:Carbocyclic analogs, Antivirals, Nucleoside phosphonates
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:61
Number:5
Page Range:pp. 778-790
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19960778UNSPECIFIED
ID Code:979
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Liboska, Radek; Masojídková, Milena; Rosenberg, Ivan (1996) Carbocyclic Phosphonate-Based Nucleotide Analogs Related to PMEA II. Racemic cis-Configured Derivatives. Collection of Czechoslovak Chemical Communications, 61 (5). pp. 778-790. ISSN 0010-0765

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