6-氨基-1-β-D-呋喃核糖基吡唑并[3,4-d]嘧啶-4-酮及相关4,6-二取代吡唑并嘧啶核苷的简便合成方法。
A convenient synthesis of 6-amino-1-beta-D-ribofuranosylpyrazolo[3,4-d]pyrimidin-4-one and related 4,6-disubstituted pyrazolopyrimidine nucleosides.
作者信息
Cottam H B, Revankar G R, Robins R K
出版信息
Nucleic Acids Res. 1983 Feb 11;11(3):871-82. doi: 10.1093/nar/11.3.871.
The glycosylation of 4,6-dichloropyrazolo[3,4-d]pyrimidine and 4-chloro-6-methylthiopyrazolo[3,4-d]pyrimidine via the corresponding trimethylsilyl intermediate and tetra-O-acetyl-beta-D-ribofuranose in the presence of trimethylsilyl triflate as a catalyst, gave selective glycosylation at N1 as the only nucleoside product. The intermediates 4,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)pyrazolo [3,4-d]pyrimidine 7 and 4-chloro-6-methylthio-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)pyrazolo [3,4-d]pyrimidine 13 gave new and convenient synthetic routes to the inosine analog 1, the guanosine analog 2, the adenosine analog 3, and the isoguanosine analog 16. Glycosylation of the trimethylsilyl derivative of 6-chloropyrazolo[3,4-d]pyrimidine-4-one unexpectedly gave the N2-glycosyl isomer 20 as the major product. A number of new 4,6-disubstituted pyrazolo[3,4-d]pyrimidine nucleosides were prepared from these glycosyl intermediates.
在三氟甲磺酸三甲基硅酯作为催化剂的存在下，4,6 - 二氯吡唑并[3,4 - d]嘧啶和4 - 氯 - 6 - 甲基硫代吡唑并[3,4 - d]嘧啶通过相应的三甲基硅基中间体与四 - O - 乙酰基 - β - D - 呋喃核糖进行糖基化反应，以N1位选择性糖基化作为唯一的核苷产物。中间体4,6 - 二氯 - 1 - (2,3,5 - 三 - O - 乙酰基 - β - D - 呋喃核糖基)吡唑并[3,4 - d]嘧啶7和4 - 氯 - 6 - 甲基硫代 - 1 - (2,3,5 - 三 - O - 乙酰基 - β - D - 呋喃核糖基)吡唑并[3,4 - d]嘧啶13为肌苷类似物1、鸟苷类似物2、腺苷类似物3和异鸟苷类似物16提供了新的便捷合成路线。6 - 氯吡唑并[3,4 - d]嘧啶 - 4 - 酮的三甲基硅基衍生物的糖基化反应意外地以N2 - 糖基异构体20作为主要产物。从这些糖基中间体制备了许多新的4,6 - 二取代吡唑并[3,4 - d]嘧啶核苷。
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