Matsuda A, Muneyama K, Nishida T, Sato T, Ueda T
Nucleic Acids Res. 1976 Dec;3(12):3349-57. doi: 10.1093/nar/3.12.3349.
A versatile method for the synthesis of 5'-deoxy-8,5'-cycloadenosine, a conformationally-fixed "anti" type of adenosine, was presented. Irradiation of 2', 3'-O-isopropylidene-5'-deoxy-5'-phenylthioadenosine with 60W Hg vapor lamp afforded 2',3'-O-isopropylidene-5'-deoxy-8,5'-cycloadenosine in high yield. The use of other 5'-alkylthio derivatives also gave the cycloadenosine, though the yields were rather poor. Deacetonation of the cyclocompound with 0.1N HCl gave 5'-deoxy-8,5'-cycloadenosine. The cycloinosine derivative was similarly prepared. The nmr, mass and CD spectra of 5'-deoxy-8,5'-cycloadenosine were given and discussed with the previously reported results.
介绍了一种合成5'-脱氧-8,5'-环腺苷的通用方法，5'-脱氧-8,5'-环腺苷是一种构象固定的“反式”腺苷类型。用60W汞蒸气灯照射2',3'-O-异丙叉基-5'-脱氧-5'-苯硫基腺苷可高产率得到2',3'-O-异丙叉基-5'-脱氧-8,5'-环腺苷。使用其他5'-烷硫基衍生物也能得到环腺苷，不过产率相当低。用0.1N盐酸使环化合物脱乙酰基得到5'-脱氧-8,5'-环腺苷。环肌苷衍生物也用类似方法制备。给出了5'-脱氧-8,5'-环腺苷的核磁共振、质谱和圆二色光谱，并与先前报道的结果进行了讨论。
