Synthesis of Acyclic Nucleotide Analogues Derived from 6-(sec- or tert-Alkyl)purines via Coupling of 6-Chloropurine Derivatives with Organocuprates

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Title:Synthesis of Acyclic Nucleotide Analogues Derived from 6-(sec- or tert-Alkyl)purines via Coupling of 6-Chloropurine Derivatives with Organocuprates
Creators:
Dvořáková, Hana
Dvořák, Dalimil
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 63, 12, pp. 2065-2074
Uncontrolled Keywords:Purines, Organocopper reagents, Acyclic nucleoside phosphonates, 6-Alkylpurines, Cross-coupling reactions, Phosphonomethoxyalkylpurine derivatives

Abstract

Coupling of 9-[2-(diisopropyloxyphosphonylmethoxy)ethyl]-6-chloropurine (<strong>23</strong>) (and (<i>R</i>)-9-[2-(diisopropyloxyphosphonylmethoxy)propyl]-6-chloropurine (<strong>24</strong>), respectively) with organocuprates derived from Grignard reagents afforded after deprotection 6-(<i>sec</i>- or <i>tert</i>-alkyl) substituted phosphonates <strong>31</strong>-<strong>36</strong>. As a model a series of 6-(<i>sec</i>- or <i>tert</i>-alkyl)purines <strong>2</strong>-<strong>12 </strong>was also prepared.

Title:Synthesis of Acyclic Nucleotide Analogues Derived from 6-(sec- or tert-Alkyl)purines via Coupling of 6-Chloropurine Derivatives with Organocuprates
Creators:
Dvořáková, Hana
Dvořák, Dalimil
Holý, Antonín
Uncontrolled Keywords:Purines, Organocopper reagents, Acyclic nucleoside phosphonates, 6-Alkylpurines, Cross-coupling reactions, Phosphonomethoxyalkylpurine derivatives
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:63
Number:12
Page Range:pp. 2065-2074
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19982065UNSPECIFIED
ID Code:1445
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:09

Citation

Dvořáková, Hana; Dvořák, Dalimil; Holý, Antonín (1998) Synthesis of Acyclic Nucleotide Analogues Derived from 6-(sec- or tert-Alkyl)purines via Coupling of 6-Chloropurine Derivatives with Organocuprates. Collection of Czechoslovak Chemical Communications, 63 (12). pp. 2065-2074. ISSN 0010-0765

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