Synthesis of ribosyl and arabinosyl cyanides by reaction of 1-O-acyl sugars with trimethylsilyl cyanide
Synthesis of ribosyl and arabinosyl cyanides by reaction of 1-O-acyl sugars with trimethylsilyl cyanide
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1-O-酰基糖与三甲基氰硅烷反应合成核糖基和阿拉伯糖基氰化物
DOI：
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发表时间：
1982
期刊：
影响因子：
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通讯作者：
P. Fernández
中科院分区：
文献类型：
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作者：
F. Heras;P. Fernández
介绍了1- o -酰基糖与三甲基硅基氰化物在极性非质子溶剂和路易斯酸催化下反应合成糖基氰化物的新工艺。各种核糖基和阿拉伯糖基氰化物都是用这种方法从糖衍生物中得到的，这些糖衍生物在端粒位置上有酰基、氯基或甲氧基离去基、呋喃糖或吡喃糖环以及酰基或苄基保护基。当起始糖有一个2- o -酰基取代基参与时，就形成了1,2-反式糖基氰化物。用不参与的苯基保护起始糖，得到了氰化物异头化合物的混合物。
A new procedure is described for the synthesis of glycosyl cyanides by reaction of 1-O-acyl sugars with trimethyl-silyl cyanide in a polar aprotic solvent and in the presence of a Lewis acid as catalyst. A variety of ribosyl and arabinosyl cyanides have been made in this way from sugar derivatives having acyl, chloro, or methoxy leaving groups at the anomeric position, furanose or pyranose rings, and acyl or benzyl protecting groups. The 1,2-Trans-glycosyl cyanide was formed when the starting sugar had a participating 2-O-acyl substituent. A mixture of cyanide anomers was obtained when the starting sugar was protected with non-participating benzyl groups.