FACILE SYNTHESIS OF 2'-AMINO-2'-DEOXYRIBOFURANOSYL PURINES
FACILE SYNTHESIS OF 2'-AMINO-2'-DEOXYRIBOFURANOSYL PURINES
复制标题
DOI：
10.1021/jo01326a037
复制
发表时间：
1979-01-01
影响因子：
3.6
通讯作者：
ECKSTEIN, F
中科院分区：
文献类型：
--
作者：
IMAZAWA, M;ECKSTEIN, F
由尿苷易得的2‘-叠氮-2’-脱氧尿苷合成了2‘’-叠氮-2‘-脱氧和2’‘-氨基-2’-脱氧呋喃核苷。它利用来自嘧啶核苷的糖部分与嘌呤碱缩合。为了进一步简化合成，研究了与嘌呤碱的直接转糖基化反应，而不是单独分离和缩合糖基。报道了以2‘’-氨基-2‘’-脱氧尿苷为原料，以较高的产率合成2‘’-氨基-2‘-脱氧腺苷和鸟苷的方法。尝试与2‘’-叠氮-2‘-脱氧尿苷的糖基化反应失败。
A convenient synthesis of 2''-azido-2''-deoxy- and 2''-amino-2''-deoxyribofuranosyl purines from 2''-azido-2''-deoxyuridine, which is readily available from uridine, was recently developed. It utilizes the sugar moiety derived from the pyrimidine nucleoside for condensation with the purine bases. To simplify the synthesis further, a direct transglycosylation reaction with purine bases was investigated instead of isolating and condensing the sugar moiety separately. The success of this approach for the synthesis of 2''-amino-2''-deoxyadenosine and -guanosine in much better yields than previously obtainable, using 2''-amino-2''-deoxyuridine as starting material is reported. An attempted transglycosylation reaction with 2''-azido-2''-deoxyuridine failed.