Synthesis of Optically Active N6-Alkyl Derivatives of (R)-3-(Adenin-9-yl)-2-hydroxypropanoic Acid and Related Compounds

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Title:Synthesis of Optically Active N6-Alkyl Derivatives of (R)-3-(Adenin-9-yl)-2-hydroxypropanoic Acid and Related Compounds
Creators:
Krečmerová, Marcela
Buděšínský, Miloš
Masojídková, Milena
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 5, pp. 931-950
Uncontrolled Keywords:Epoxides, Purines, <i>S</i>-Adenosyl-L-homocysteine hydrolase inhibitors, Nucleosides, Enantiomeric purity determination, Antivirals, Oxirane ring opening, Adenine, SAH hydrolase, Acyclic nucleoside analogues

Abstract

Reaction of ethyl (<i>R</i>)-oxiranecarboxylate (<strong>2a</strong>) with various nucleobases (adenine, 6-chloropurine, thymine, cytosine, <i>N</i><sup>6</sup>-benzoyladenine, 4-methoxy-5-methylpyrimidin-2(1<i>H</i>)-one and 4-methoxypyrimidin-2(1<i>H</i>)-one) afforded ethyl 3-substituted-2-hydroxypropanoates <strong>4</strong>-<strong>10</strong>. Enantioselectivity of this reaction is dependent on the type of the base: 6-chloropurine, <i>N</i><sup>6</sup>-benzoyladenine, 4-methoxy-5-methylpyrimidin-2(1<i>H</i>)-one, thymine and cytosine gave optically pure <i>R</i> enantiomers. In other cases, partial or complete racemization occurred. Optically pure ethyl (<i>R</i>)-3-(6-chloropurin-9-yl)-2-hydroxypropanoate (<strong>5a</strong>) was hydrolyzed to give (<i>R</i>)-3-(6-chloropurin-9-yl)-2-hydroxypropanoic acid (<strong>11</strong>). Reactions of <strong>11</strong> with various primary or secondary amines led to <i>N</i><sup>6</sup>-substituted (<i>R</i>)-3-(adenin-9-yl)-2-hydroxypropanoic acids <strong>14</strong>-<strong>19</strong>. Enantiomeric purity was determined from <sup>1</sup>H NMR spectra measured in the presence of (-)-(<i>R</i>)-1-(9-anthryl)-2,2,2-trifluoroethan-1-ol. <p>

Title:Synthesis of Optically Active N6-Alkyl Derivatives of (R)-3-(Adenin-9-yl)-2-hydroxypropanoic Acid and Related Compounds
Creators:
Krečmerová, Marcela
Buděšínský, Miloš
Masojídková, Milena
Holý, Antonín
Uncontrolled Keywords:Epoxides, Purines, <i>S</i>-Adenosyl-L-homocysteine hydrolase inhibitors, Nucleosides, Enantiomeric purity determination, Antivirals, Oxirane ring opening, Adenine, SAH hydrolase, Acyclic nucleoside analogues
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:68
Number:5
Page Range:pp. 931-950
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20030931UNSPECIFIED
ID Code:2095
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Krečmerová, Marcela; Buděšínský, Miloš; Masojídková, Milena; Holý, Antonín (2003) Synthesis of Optically Active N6-Alkyl Derivatives of (R)-3-(Adenin-9-yl)-2-hydroxypropanoic Acid and Related Compounds. Collection of Czechoslovak Chemical Communications, 68 (5). pp. 931-950. ISSN 0010-0765

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