GENERAL METHOD FOR SYNTHESIS OF 2'-AZIDO-2'-DEOXY AND 2'-AMINO-2'-DEOXYRIBOFURANOSYL PURINES
GENERAL METHOD FOR SYNTHESIS OF 2'-AZIDO-2'-DEOXY AND 2'-AMINO-2'-DEOXYRIBOFURANOSYL PURINES
复制标题
DOI：
10.1021/jo00424a031
复制
发表时间：
1977-01-01
影响因子：
3.6
通讯作者：
ECKSTEIN, F
中科院分区：
文献类型：
--
作者：
HOBBS, JB;ECKSTEIN, F
用水合肼处理2“-叠氮基-2”-脱氧尿苷，随后用苯甲醛在沸腾的水中处理产物，得到2-叠氮基-2-脱氧核糖，通过标准方法将其衍生为1，3，5-三乙酸酯（7）。7与N6-辛酰基腺嘌呤缩合，随后脱酰，得到α的混合物。和β2“-叠氮基-2”-脱氧腺苷的异头体（8a和8b），其可在Dowex 1X上分离。2（OH-）。用N2-棕榈酰基鸟嘌呤代替N6-辛酰基腺嘌呤得到产物的混合物，其中7-和9-（2-叠氮基-2-脱氧-β-氨基）-N-（2-叠氮基-2-脱氧-氨基）-N-（2-叠氮基）-N- D-呋喃核糖基）鸟嘌呤（11b和10 b）可通过分步结晶分离。α似乎也形成了端基异构体，但尚未分离。用三苯基膦和NH_3还原8a、8b、10 b和11 b，以良好的产率得到相应的2 ″-氨基-2 ″-脱氧核苷。
Treatment of 2''-azido-2''-deoxyuridine with hydrazine hydrate and subsequent treatment of the products with benzaldehyde in boiling H2O affords 2-azido-2-deoxyribose, which is derivatized by standard methods to the 1,3,5-triacetate (7). Condensation of 7 with N6-octanoyladenine and subsequent deacylation affords a mixture of .alpha. and .beta. anomers of 2''-azido-2''-deoxyadenosine (8a and 8b) which is separable on Dowex 1 .times. 2 (OH-). Replacement of N6-octanoyladenine by N2-palmitoylguanine affords a mixture of products from which 7- and 9-(2-azido-2-deoxy-.beta.-D-ribofuranosyl)guanine (11b and 10b) are isolable by fractional crystallization. The .alpha. anomers also appear to be formed, but have not yet been isolated. Reduction of 8a, 8b, 10b and 11b with triphenylphosphine and NH3 affords the corresponding 2''-amino-2''-deoxy nucleosides in good yield.