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Syntheses of 2′-deoxy-2′-fluoro-β-d-arabinofuranosyl purine nucleosides via selective glycosylation reactions of potassium salts of purine derivatives with the glycosyl bromide
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2015-12-31 02:49:23 Grigorii G. Sivets
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2015-12-31 02:49:23 Grigorii G. Sivets
Syntheses of 9-(2-deoxy-2-fluoro-β-d-arabinofuranosyl)-guanine (1) and -adenine (2) were accomplished from readily available 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-d-arabinofuranose (3). A new and efficient approach for the synthesis of 1-α-bromide was developed using the mild bromination of α-1-O-benzoate (3). Selective coupling reactions of the bromosugar with purine potassium salts followed by derivatization/and or deprotection of the intermediate blocked 2′-fluoro β-arabinonucleosides resulted in formation of the target compounds with high overall yields.
中文翻译:
通过嘌呤衍生物的钾盐与糖基溴化物的选择性糖基化反应合成2'-脱氧-2'-氟-β-d-阿拉伯呋喃糖基嘌呤核苷
9-(2-脱氧-2-氟-β-d-阿拉伯呋喃糖基)-鸟嘌呤(1)和-腺嘌呤(2)的合成是由容易获得的1,3,5-三-O-苯甲酰基-2-脱氧完成的-2-氟-α-d-阿拉伯呋喃糖(3)。利用α-1-O-苯甲酸酯的温和溴化作用,开发了一种新的高效合成1-α-溴化物的方法(3)。溴糖与嘌呤钾盐的选择性偶联反应,然后对中间体封闭的2'-氟β-阿拉伯糖核苷进行衍生化和/或去保护,导致形成具有高总收率的目标化合物。
更新日期:2015-12-31
中文翻译:
通过嘌呤衍生物的钾盐与糖基溴化物的选择性糖基化反应合成2'-脱氧-2'-氟-β-d-阿拉伯呋喃糖基嘌呤核苷
9-(2-脱氧-2-氟-β-d-阿拉伯呋喃糖基)-鸟嘌呤(1)和-腺嘌呤(2)的合成是由容易获得的1,3,5-三-O-苯甲酰基-2-脱氧完成的-2-氟-α-d-阿拉伯呋喃糖(3)。利用α-1-O-苯甲酸酯的温和溴化作用,开发了一种新的高效合成1-α-溴化物的方法(3)。溴糖与嘌呤钾盐的选择性偶联反应,然后对中间体封闭的2'-氟β-阿拉伯糖核苷进行衍生化和/或去保护,导致形成具有高总收率的目标化合物。