Synthesis of 9-(2-Phosphinomethoxyethyl)adenine and Related Compounds
1994 ◽
Vol 59
(8)
◽
pp. 1870-1878
◽
Keyword(s):
Alkyl 2-chloroethoxymethyl(diethoxymethyl)phosphinates VII and XIII were prepared by reaction of silyl esters of dialkoxymethylphosphinic acid with 2-chloroethyl chloromethyl ether. Adenine was alkylated with VII and XIII to give [2-(adenin-9-yl)ethoxy]methyl(diethoxymethyl)phosphinates VIII and XIV, bearing the dialkoxymethyl protecting group on the phosphorus atom. Acid hydrolysis of compounds VIII and XIV afforded 9-(2-phosphinoethoxymethyl)adenine (X). Alkyl dialkoxymethylphosphinates V and XI reacted with paraformaldehyde to give hydroxymethylphosphinates XV and XIX which were converted into the synthons XVI, XVII and XVIII capable of introducing a protected hydroxymethylphosphino group on a hydroxy or amino group.
1992 ◽
pp. 213-217
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1973 ◽
Vol 74
(6)
◽
pp. 1083-1089
◽
1994 ◽
Vol 59
(3)
◽
pp. 667-674
◽
Synthesis of Some 2'-C-Alkyl Derivatives of 9-(2-Phosphonomethoxyethyl)adenine and Related Compounds
1994 ◽
Vol 59
(9)
◽
pp. 2069-2094
◽
1968 ◽
Vol 23
(10)
◽
pp. 1319-1325
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Keyword(s):