2',3'-Dideoxy- and 3'-Azido-2',3'-dideoxynucleosides of 5-Phenyl-2(1H)-pyrimidinone. Preparation of 2',3'-Dideoxypentofuranoses

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Title:2',3'-Dideoxy- and 3'-Azido-2',3'-dideoxynucleosides of 5-Phenyl-2(1H)-pyrimidinone. Preparation of 2',3'-Dideoxypentofuranoses
Creators:
Krečmerová, Marcela
Hřebabecký, Hubert
Masojídková, Milena
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 3, pp. 478-488
Uncontrolled Keywords:Sugar-modified, Nucleosides, Pyrimidine, AZT analogs, Dideoxynucleosides, 5-Phenyl-2(1<i>H</i>)-pyrimidinone

Abstract

The synthesis of methyl 3-azido-5-benzoyl-2,3-dideoxy-β-D-ribofuranoside (<strong>10</strong>) from methyl 2-deoxy-D-ribofuranoside (<strong>1</strong>) and its use for the preparation of 3'-azido-2',3'-dideoxy-β-D-ribofuranosides is described. Reaction of methylglucoside <strong>1</strong> with benzoyl chloride in pyridine afforded 5-<i>O</i>-benzoyl derivative <strong>2</strong>, which on oxidation with complex of chromium trioxide, pyridine and acetic anhydride afforded 3-keto derivative <strong>3</strong>. This was reduced with sodium borohydride in ethanol to give a mixture of methyl 2-deoxyglycosides of α-D-<i>ribo</i>- (<strong>4</strong>) and β-D-<i>xylo</i>- (<strong>5</strong>) configuration. Their mesyl derivatives <strong>6</strong> and <strong>7</strong> were chromatographically separated. Compound <strong>7</strong> reacted with sodium azide in hot dimethylformamide to afford methyl 3-azido-5-<i>O</i>-benzoyl-2,3-dideoxy-β-D-ribofuranoside (<strong>10</strong>). 5-Phenyl-2(1<i>H</i>)-pyrimidinone was converted into silyl derivative <strong>11</strong> by treatment with hexamethyldisilazane. Reaction of compound <strong>11</strong> with the azido sugar <strong>10</strong>, catalyzed by trimethylsilyl trifluoromethanesulfonate, and subsequent methanolysis, furnished a mixture of anomeric 3'-azido-2',3'-dideoxynucleosides <strong>14</strong> and <strong>15</strong>. Methyl 5-<i>O</i>-benzoyl-2,3-dideoxy-α-D-ribofuranoside (<strong>17</strong>) was prepared from methyl-α-glycoside <strong>4</strong> by reaction with thionyl chloride and subsequent reduction of the obtained 3-chloro derivative <strong>16</strong> with tributylstannane. Silyl derivative <strong>11</strong> reacted with 2,3-dideoxy sugar <strong>17</strong> under catalysis with trimethylsilyl triflate to give mainly 1-(5-<i>O</i>-benzoyl-2,3-dideoxy-α-D-<i>glycero</i>-pentofuranosyl)-5-phenyl-2(1<i>H</i>)-pyrimidinone (<strong>19</strong>) and minor amount of the β-anomer <strong>18</strong>. Their methanolysis afforded dideoxynucleosides <strong>20</strong> and <strong>21</strong>.

Title:2',3'-Dideoxy- and 3'-Azido-2',3'-dideoxynucleosides of 5-Phenyl-2(1H)-pyrimidinone. Preparation of 2',3'-Dideoxypentofuranoses
Creators:
Krečmerová, Marcela
Hřebabecký, Hubert
Masojídková, Milena
Holý, Antonín
Uncontrolled Keywords:Sugar-modified, Nucleosides, Pyrimidine, AZT analogs, Dideoxynucleosides, 5-Phenyl-2(1<i>H</i>)-pyrimidinone
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:3
Page Range:pp. 478-488
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19960478UNSPECIFIED
ID Code:950
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Krečmerová, Marcela; Hřebabecký, Hubert; Masojídková, Milena; Holý, Antonín (1996) 2',3'-Dideoxy- and 3'-Azido-2',3'-dideoxynucleosides of 5-Phenyl-2(1H)-pyrimidinone. Preparation of 2',3'-Dideoxypentofuranoses. Collection of Czechoslovak Chemical Communications, 61 (3). pp. 478-488. ISSN 0010-0765

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