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

Synthesis of 9-(2-Phosphinomethoxyethyl)adenine and Related Compounds
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9-(2-膦基甲氧基乙基)腺嘌呤及相关化合物的合成

DOI：
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发表时间：
1987
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影响因子：
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通讯作者：
M. Masojídková
M. Masojídková
中科院分区：
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文献类型：
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作者：
P. Alexander;A. Holý;M. Masojídková

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以二氧甲基膦酸硅酯与2-氯乙基氯甲基醚为原料，制备了2-氯乙氧基甲基（二氧基甲基）膦酸酯VII和XIII。腺嘌呤与VII和XIII烷基化得到[2-（腺嘌呤-9-基）乙氧基]甲基（二氧基甲基）膦酸盐VIII和XIV，磷原子上有二氧基甲基保护基团。化合物VIII和XIV的酸水解得到9-（2-磷酸乙氧基甲基）腺嘌呤(X)。烷基二氧甲基膦酸盐V和XI与多聚甲醛反应生成羟甲基膦酸盐XV和XIX，它们转化为合成子XVI， XVII和XVIII，这些合成子能够在羟基或氨基上引入受保护的羟甲基膦基。
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.