Efficient syntheses of β-cyanosugars using glycosyl iodides derived from per-O-silylated mono- and disaccharides
Efficient syntheses of β-cyanosugars using glycosyl iodides derived from per-O-silylated mono- and disaccharides
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DOI：
10.1021/ol0160405
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发表时间：
2001-06-28
期刊：
影响因子：
5.2
通讯作者：
Gervay-Hague, J
中科院分区：
文献类型：
--
作者：
Bhat, AS;Gervay-Hague, J
【图】本文报道了一种通过TMSI活化对o -三甲基基糖苷，生成α -糖基碘化物，高效合成多种β -氰基糖苷的一般方法，经四丁基氰化铵处理后发生S(N)2型位移。在温和条件下，用NaBH4在THF/H2O中催化CoCl2(H2O)(6)的存在下还原得到相应的氨基甲基糖苷。
[GRAPHICS]Reported herein is a general method for the efficient syntheses of a variety of beta -cyano glycosides through the activation of per-O-trimethylsllyl glycosides with TMSI to form alpha -glycosyl iodides, which undergo S(N)2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)(6) in THF/H2O to give the corresponding aminomethyl glycosides.