Synthesis of 9-(2-Phosphinomethoxyethyl)adenine and Related Compounds

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Title:Synthesis of 9-(2-Phosphinomethoxyethyl)adenine and Related Compounds
Creators:
Alexander, Petr
Holý, Antonín
Masojídková, Milena
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 8, pp. 1870-1878

Abstract

<p>Alkyl 2-chloroethoxymethyl(diethoxymethyl)phosphinates <i>VII</i> and <i>XIII</i> were prepared by reaction of silyl esters of dialkoxymethylphosphinic acid with 2-chloroethyl chloromethyl ether. Adenine was alkylated with <i>VII</i> and <i>XIII</i> to give [2-(adenin-9-yl)ethoxy]methyl(diethoxymethyl)phosphinates <i>VIII</i> and <i>XIV</i>, bearing the dialkoxymethyl protecting group on the phosphorus atom. Acid hydrolysis of compounds <i>VIII</i> and <i>XIV</i> afforded 9-(2-phosphinoethoxymethyl)adenine (<i>X</i>). Alkyl dialkoxymethylphosphinates <i>V</i> and <i>XI</i> reacted with paraformaldehyde to give hydroxymethylphosphinates <i>XV</i> and <i>XIX</i> which were converted into the synthons <i>XVI</i>, <i>XVII</i> and <i>XVIII</i> capable of introducing a protected hydroxymethylphosphino group on a hydroxy or amino group.

Title:Synthesis of 9-(2-Phosphinomethoxyethyl)adenine and Related Compounds
Creators:
Alexander, Petr
Holý, Antonín
Masojídková, Milena
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:59
Number:8
Page Range:pp. 1870-1878
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19941870UNSPECIFIED
ID Code:610
Item Type:Article
Deposited On:06 Feb 2009 17:02
Last Modified:06 Feb 2009 16:02

Citation

Alexander, Petr; Holý, Antonín; Masojídková, Milena (1994) Synthesis of 9-(2-Phosphinomethoxyethyl)adenine and Related Compounds. Collection of Czechoslovak Chemical Communications, 59 (8). pp. 1870-1878. ISSN 0010-0765

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