Ostrowski T, Zeidler J, Goslinski T, Golankiewicz B
Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznan.
Nucleosides Nucleotides Nucleic Acids. 2000 Oct-Dec;19(10-12):1911-29. doi: 10.1080/15257770008045468.
Aryl or tert-butyl substituent in the 6 position of 3,9-dihydro-3-[(2-hydroxyethoxy)methyl]-9-oxo-6-R-5H-imidazo[1,2-a]purine (6-R-TACV) 1 partly directs aralkylation reactions into unusual positions: N-4 to give 3 and C-7 to give N-5,7-disubstituted or N-4,7-disubstituted derivatives. In the case of alkylation the effect is limited to aryl substituent and position N-4. Replacement of acyclic moiety of 1 with a ribosyl one like in 7 prevents N-4 substitution. Cleavage of the third ring of 3b to give 3-benzylacyclovir 10 is an example of a new short route to 3-aralkyl-9-substituted guanines.
3,9-二氢-3-[(2-羟基乙氧基)甲基]-9-氧代-6-R-5H-咪唑并[1,2-a]嘌呤(6-R-TACV)1的6位上的芳基或叔丁基取代基部分地将芳烷基化反应导向异常位置：N-4生成3，C-7生成N-5,7-二取代或N-4,7-二取代衍生物。在烷基化的情况下，这种作用仅限于芳基取代基和N-4位。用如7中的核糖基部分取代1的无环部分可防止N-4取代。将3b的第三个环裂解生成3-苄基阿昔洛韦10是一条合成3-芳烷基-9-取代鸟嘌呤的新的短路线的一个例子。
