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Stereoselective synthesis of 9-b-D-arabianofuranosyl guanine and 2-amino-9-(b-D-arabianofuranosyl)purine
余学军 / 邓友全
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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-p-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 P-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.

★★★☆☆ X.-J. Yu et al. / Bioorg. Med. Chem. Lett. 15 (2005) 683–685.