Use of Ferric Chloride in Carbohydrate Reactions.1 Iv. Acetolysis of Benzyl Ethers of Sugars
Use of Ferric Chloride in Carbohydrate Reactions.1 Iv. Acetolysis of Benzyl Ethers of Sugars
复制标题
氯化铁在碳水化合物反应中的用途。1 IV．
DOI：
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发表时间：
1986
期刊：
影响因子：
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通讯作者：
H. Srivastava
中科院分区：
文献类型：
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作者：
K. Kartha;F. Dasgupta;P. Singh;H. Srivastava
摘要本文研究了无水氯化铁在乙酸酐中对糖的苄醚的乙酰解反应。通过使用该试剂，可以容易地去除位于糖或其糖苷中的各种苄基醚基团并被乙酰基取代。通过控制乙酰解，可以优先除去某些苄基。结果表明，D-葡萄糖中苄醚基的乙酰解脱除的相对容易程度为C-6 > C-4 > C-3 > C-2，乙酰解速率为6-O-Bn：3-O-Bn：2-O-Bn = 125：24：1。相应的甲基醚对乙酰化反应非常缓慢。
Abstract Acetolysis of benzyl ethers of sugars has been carried out with anhydrous ferric chloride in acetic anhydride. By employing this reagent, benzyl ether groups variously placed in sugars or in their glycosides could be removed with ease and replaced by acetyl groups. By controlled acetolysis, preferential removal of certain benzyl groups was possible. The results show that in D-glucose the relative ease of removal of benzyl ether groups by acetolysis follows the order C-6 > C-4 > C-3 > C-2 and that the rate of acetolysis is 6-O-Bn : 3-O-Bn : 2-O-Bn = 125 : 24 : 1. The corresponding methyl ethers were very sluggish towards acetolysis.