1,2-cis-Selective glucosylation enabled by halogenated benzyl protecting groups,Organic & Biomolecular Chemistry

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1,2-cis-Selective glucosylation enabled by halogenated benzyl protecting groups
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020/03/10 , DOI: 10.1039/d0ob00373e
Dancan K. Njeri _{1,

2,

3,

4} , Claude J. Pertuit _{1,

2,

3,

4} , Justin R. Ragains _{1,

2,

3,

4}

Affiliation

We report on our initial results from a systematic effort to implement electron-withdrawing protecting groups and Lewis basic solvents/additives as an approach to 1,2-cis(α)-selective O-glucosylation. 1,2-cis-Selective O-glucosylations are reported with thioglucosides and glucosyl trichloroacetimidates and a range of acceptors. A correlation between electron-withdrawing effects and 1,2-cis selectivity has been established. This phenomenon may prove to be broadly applicable in the area of chemical O-glycosylation.

中文翻译：

卤代苄基保护基团可实现1,2-顺式选择性糖基化

我们报告了我们的初步结果，这是系统地实施吸电子保护基团和Lewis碱性溶剂/添加剂作为1,2-顺式（α）-选择性O-葡萄糖基化方法的结果。据报道，硫代葡糖苷和葡糖基三氯乙酰亚氨酸酯和一系列受体具有1，2-顺式选择性O-葡糖基化。已经建立了吸电子效应与1,2-顺式选择性之间的相关性。该现象可能被证明可广泛用于化学O-糖基化领域。

更新日期：2020-04-01

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