Synthesis of 8-alkyladenosines, 8,2'-anhydro-8-hydroxymethyl-9-(β-D-arabinofuranosyl)adenine and related compounds (nucleosides and nucleotides. LVIII)
Synthesis of 8-alkyladenosines, 8,2'-anhydro-8-hydroxymethyl-9-(β-D-arabinofuranosyl)adenine and related compounds (nucleosides and nucleotides. LVIII)
复制标题
8-烷基腺苷、8,2-脱水-8-羟甲基-9-(β-D-阿拉伯呋喃糖基)腺嘌呤及相关化合物（核苷和核苷酸。LVIII）的合成
DOI：
10.1248/cpb.33.3263
复制
发表时间：
1985
影响因子：
1.7
通讯作者：
A. Matsuda
中科院分区：
文献类型：
--
作者：
T. Ueda;Y. Nomoto;A. Matsuda
描述了8-烷基腺苷和相关核苷的合成。5 ′-O-乙酰基-2 ′，3 ′-O-异亚丙基-8-甲磺酰基腺苷与二乙酰乙酸乙酯反应，得到8-乙氧羰基甲基衍生物（1）。1水解脱羧、脱丙酮得8-甲基腺苷（2）。1与甲基或乙基碘烷基化，然后水解脱羧，分别得到8-乙基和8-丙基腺苷。尝试将1的8-亚甲基二甲基化导致形成N6-二甲基腺苷衍生物。2 '-脱氧腺苷和2'-脱氧胞苷的氨基的选择性二甲基化已经通过使用碘甲烷和氢化钠的组合而实现，而这些核苷的糖羟基没有甲基化。以8-氰基腺苷衍生物为起始原料，通过8-羟甲基-2 '-耳磺腺苷的碱处理形成脱水键，合成了8，2'-脱水-9-β-D-阿拉伯呋喃糖基-8-羟甲基腺嘌呤。讨论了8-烷基腺苷类化合物的圆二色光谱特性。
Synthesis of 8-alkyladenosines and related nucleosides is described. Treatment of 5'-O-acetyl-2', 3'-O-isopropylidene-8-methylsulfonyladenosine with ethyl sodioacetoacetate gave the 8-ethoxy-carbonylmethyl derivative (1). Hydrolytic decarboxylation of 1 followed by deacetonation afforded 8-methyladenosine (2) in high yield. Alkylation of 1 with methyl or ethyl iodide followed by hydrolytic decarboxylation afforded 8-ethyl- and 8-propyladenosines, respectively. Attempts at dimethylation of the 8-methylene group of 1 resulted in the formation of the N6-dimethyladenosine derivative. Selective dimethylation of the amino groups of 2'-deoxyadenosine and 2'-deoxycytidine has been accomplished by using a combination of methyl iodide and sodium hydride without methylation of the sugar hydroxyl groups of these nucleosides. 8, 2'-Anhydro-9-β-D-arabinofuranosyl-8-hydroxymethyladenine was prepared from a 8-cyanoadenosine derivative by the procedure involving anhydro-bond formation by base treatment of 8-hydroxymethyl-2'-Otosyladenosine. The circular dichroism spectral characteristics of 8-alkyladenosines are discussed.