Reaction of Glyconitriles with Organometallic Reagents: Access to Acyl β-C-Glycosides

Reaction of Glyconitriles with Organometallic Reagents: Access to Acyl β-C-Glycosides
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DOI:
10.1021/acs.joc.5b02853
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发表时间:
2016-03-18
影响因子:
3.6
通讯作者:
Guillarme, Stephane
Guillarme, Stephane
中科院分区:
化学2区
文献类型:
--
作者:
Guisot, Nicolas E. S.;Obame, Idriss Ella;Guillarme, Stephane

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A new strategy for the synthesis of acyl beta-C-glycosides is described. The reactivity of glyconitriles toward organometallic reagents such as organomagnesium or organolithium derivatives was studied, affording acyl beta-C-glycosides in moderate to good yields. In this study, glycal formation was efficiently prevented by deprotonating the hydroxyl group in position 2 of the glyconitriles during the process.