Synthesis of Racemic 2-Hydroxy-4- and 2-Hydroxy-5-(hydroxymethyl)cyclohexane Nucleoside Analogues

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Title:Synthesis of Racemic 2-Hydroxy-4- and 2-Hydroxy-5-(hydroxymethyl)cyclohexane Nucleoside Analogues
Creators:
Hřebabecký, Hubert
Masojídková, Milena
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 11, pp. 1681-1699
Uncontrolled Keywords:Epoxides, Nucleosides, Thymine, Antivirals, Cyclohexanes, Carbanucleosides, Adenine, Carbocyclic nucleosides, NMR spectroscopy

Abstract

New racemic 2-hydroxy-4- and 2-hydroxy-5-(hydroxymethyl)cyclohexane analogues of adenine (<strong>10b</strong> and <strong>16b</strong>) and thymine nucleosides (<strong>13b</strong> and <strong>19b</strong>) were prepared by alkylation of 1,8-diazabicyclo[5.4.0]undec-7-ene salt of adenine and/or thymine with 3-vinyl-7-oxabicyclo[4.1.0]heptane followed by cis hydroxylation with osmium(VIII) oxide and sodium chlorate, oxidation with sodium periodate, and borohydride reduction. <p>

Title:Synthesis of Racemic 2-Hydroxy-4- and 2-Hydroxy-5-(hydroxymethyl)cyclohexane Nucleoside Analogues
Creators:
Hřebabecký, Hubert
Masojídková, Milena
Holý, Antonín
Uncontrolled Keywords:Epoxides, Nucleosides, Thymine, Antivirals, Cyclohexanes, Carbanucleosides, Adenine, Carbocyclic nucleosides, NMR spectroscopy
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:67
Number:11
Page Range:pp. 1681-1699
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20021681UNSPECIFIED
ID Code:2026
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:15

Citation

Hřebabecký, Hubert; Masojídková, Milena; Holý, Antonín (2002) Synthesis of Racemic 2-Hydroxy-4- and 2-Hydroxy-5-(hydroxymethyl)cyclohexane Nucleoside Analogues. Collection of Czechoslovak Chemical Communications, 67 (11). pp. 1681-1699. ISSN 0010-0765

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