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9-β-D-阿拉伯呋喃糖基鸟嘌呤和2-氨基-9-(β-D-阿拉伯呋喃糖基)嘌呤的立体选择性合成。

Stereoselective synthesis of 9-beta-d-arabianofuranosyl guanine and 2-amino-9-(beta-d-arabianofuranosyl)purine.

作者信息

Yu Xue-Jun, Li Gai-Xia, Qi Xiou-Xiang, Deng You-Quan

机构信息

Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China.

出版信息

Bioorg Med Chem Lett. 2005 Feb 1;15(3):683-5. doi: 10.1016/j.bmcl.2004.11.029.

Abstract

9-beta-d-Arabianofuranosyl guanine (6) and 2-amino-9-(beta-d-arabianofuranosyl)purine (8) were prepared from 2-amino-6-chloro-9-(2,3,5-triphenylmethoxyl-beta-d-arabianofuranosyl)purine (4), a key intermediate which was stereoselectively prepared from 2,3,5-triphenylmethoxyl-d-arabianofuranose and 2-amino-6-chloro-purine. The yield of the intermediate was obviously improved and only beta-isomer was formed by using the activated molecular sieve as environmental friendly catalyst, overcoming the defect that a 1:1 mixture of alpha- and beta-isomers was formed, which was difficult to separate, when toxic mercury cyanide was previously used as catalyst.

摘要

9-β-D-阿拉伯呋喃糖基鸟嘌呤(6)和2-氨基-9-(β-D-阿拉伯呋喃糖基)嘌呤(8)由2-氨基-6-氯-9-(2,3,5-三苯基甲氧基-β-D-阿拉伯呋喃糖基)嘌呤(4)制备而成,4是一个关键中间体,它由2,3,5-三苯基甲氧基-D-阿拉伯呋喃糖和2-氨基-6-氯嘌呤立体选择性合成。使用活性分子筛作为环境友好型催化剂,中间体的产率明显提高,且仅形成β-异构体,克服了以前使用有毒的氰化汞作为催化剂时会形成难以分离的α-异构体和β-异构体1:1混合物的缺陷。

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