Regioselective Activation of Glycosyl Acceptors by a Diarylborinic Acid-Derived Catalyst
Regioselective Activation of Glycosyl Acceptors by a Diarylborinic Acid-Derived Catalyst
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DOI：
10.1021/ja2062715
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发表时间：
2011-09-07
影响因子：
15
通讯作者：
Taylor, Mark S.
中科院分区：
文献类型：
--
作者：
Gouliaras, Christina;Lee, Doris;Taylor, Mark S.
一种二苯基硼酸酯衍生物促进带有多个仲羟基的碳水化合物衍生物的催化的、区域选择性的柯尼希斯-克诺尔糖基化。强有力的水平的选择性赤道OH基团的顺式-1，2-二醇基序的反应中证明了七个受体来自半乳糖，甘露糖，岩藻糖，阿拉伯糖使用各种糖基卤化物供体。催化剂控制提供了一种从未保护或最低限度保护的碳水化合物原料产生确定的糖苷键的新方法。
A derivative of diphenylborinic add promotes catalytic, regioselective Koenigs-Knorr glycosylations of carbohydrate derivatives bearing multiple secondary hydroxyl groups. Robust levels of selectivity for the equatorial OH group of cis-1,2-diol motifs are demonstrated in reactions of seven acceptors derived from galactose, mannose, fucose, and arabinose using a variety of glycosyl halide donors. Catalyst control presents a new means of generating defined glycosidic linkages from unprotected or minimally protected carbohydrate feedstocks.