Stereospecific synthesis of alpha-anomeric pyrimidine nucleoside.

K Shinozuka, N Matsumoto, A Nakamura, H Hayashi, H Sawai
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引用次数: 1

Abstract

A facile stereospecific synthetic method for alpha-anomeric 2'-deoxypyrimidine nucleoside unit utilizing aminooxazoline derivative of ribofuranose was investigated. Thus, easily accessible riboaminooxazoline derivative prepared by ribose and cyanamid was allowed to react with ethyl alpha-bromoethylacrylate to give corresponding adduct. The adduct was cyclized by strong base such as potassium t-butokiside. The resulted 2,2'-cyclonucleoside was then treated with acetyl bromide followed by n-butyltin hydride to give alpha-anomeric 3',5'-di-O-acetylthymidine. 3',5'-Di-O-acety groups of the nucleoside were easily removed by the action of excess of triethyl amine in methanol. Essentially same procedure afforded corresponding 2'-deoxyuridine, which was further, converted to alpha-anomeric 2'-deoxycytidine.

α -端粒嘧啶核苷的立体定向合成。
研究了一种利用核呋喃糖氨基恶唑啉衍生物立体定向合成α - 2′-脱氧嘧啶核苷元的简便方法。因此,由核糖和氰酰胺制备的易获得的核糖氨基恶唑啉衍生物可与α -溴乙基丙烯酸酯反应生成相应的加合物。加合物被t-丁托基酸钾等强碱环化。得到的2,2'-环核苷再用乙酰溴和正丁基氢化锡处理,得到α - 3',5'-二- o -乙酰胸苷。在甲醇中过量的三乙胺的作用下,核苷的3′,5′-二氧基很容易被去除。基本相同的过程得到相应的2'-脱氧尿苷,进一步转化为α - 2'-脱氧胞苷。
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