Synthesis, NMR, and conformational studies of fucoidan fragments.: III.: Effect of benzoyl group at O-3 on stereoselectivity of glycosylation by 3-O- and 3,4-di-O-benzoylated 2-O-benzylfucosyl bromides
Synthesis, NMR, and conformational studies of fucoidan fragments.: III.: Effect of benzoyl group at O-3 on stereoselectivity of glycosylation by 3-O- and 3,4-di-O-benzoylated 2-O-benzylfucosyl bromides
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DOI：
10.1081/car-100108659
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发表时间：
2001-01-01
影响因子：
1
通讯作者：
Nifantiev, NE
中科院分区：
文献类型：
--
作者：
Gerbst, AG;Ustuzhanina, NE;Nifantiev, NE
通过直接化学实验和计算化学研究了O-3位苯甲酰基对3-O-和3，4-二-O-苯甲酰基化2-O-苄基-L-吡喃岩藻糖基溴化反应立体选择性的影响。岩藻糖基供体的O-3处的苯甲酰基的影响显示出比O-4处的苯甲酰基对α-岩藻糖基化的效率具有更大的影响。假设这是O-3位苯甲酰基参与糖基阳离子稳定化的能力的结果。
The effect of a benzoyl group at O-3 on stereoselectivity of glycosylation by 3-O- and 3,4-di-O-benzoylated 2-O-benzyl-L-fucopyranosyl bromides was studied by direct chemical experiments and computational chemistry. The influence of a benzoyl group at O-3 of the fucosyl donors was shown to have a larger effect on the efficiency of alpha-fucosylation than a benzoyl group at O-4. It is hypothesized that this is a result of the ability of a benzoyl group at O-3 to participate in glycosyl cation stabilization.