Dehydrative glycosylation in water using a bronsted acid-surfactant-combined catalyst
Dehydrative glycosylation in water using a bronsted acid-surfactant-combined catalyst
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DOI：
10.1246/cl.2006.238
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发表时间：
2006-02-05
影响因子：
1.6
通讯作者：
Kobayashi, S
中科院分区：
文献类型：
--
作者：
Aoyama, N;Kobayashi, S
以十二烷基苯磺酸（DBSA）为催化剂，Br nsted酸-表面活性剂复合催化剂，在水中催化脱水糖基化反应。1-羟基糖，如O-苄基保护的呋喃糖和吡喃糖，在催化量的DBSA存在下与醇和氮亲核试剂反应，以良好的产率得到所需的加合物。对2-脱氧-D-呋喃核糖糖基化的详细研究表明，底物的疏水性对于获得更高的产率是重要的。关于α/β选择性，D-核糖和D-甘露糖衍生物分别以高β-和α-选择性得到产物。
Br phi nsted acid-surfactant-combined catalyst, dodecylbenzenesuffonic acid (DBSA), was used in catalytic dehydrative glycosylation reactions in water. I-Hydroxy sugars, such as O-benzyl-protected furanose and pyranose, reacted with alcohols and a nitrogen nucleophile in the presence of a catalytic amount of DBSA to afford the desired adducts in good yields. Detailed study of the glycosylation of 2-deoxy-D-ribofuranose showed that hydrophobicity of the substrates was important to attain higher yields. Regarding the alpha/beta selectivities, D-ribose and D-mannose derivatives gave the products in high beta- and alpha-selectivities, respectively.