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Tunable Approach for the Stereoselective Synthesis of 1-<i>C</i>-Diethylphosphono(difluoromethyl) Iminosugars as Glycosyl Phosphate Mimics

DOIFull Paper Access

30

Citations

38

References

2017

Year

Chloé Cocaud, Cyril Nicolas, Thomas Poisson, Xavier Pannecoucke, Claude Y. Legault, Olivier R. Martin
The Journal of Organic Chemistry

Abstract

An efficient methodology for the stereoselective and tunable addition of LiCF<sub>2</sub>P(O)(OEt)<sub>2</sub> and BrMgCF<sub>2</sub>P(O)(OEt)<sub>2</sub> reagents to N-t-butanesulfinyl glycosylamines is described with details on the stereochemical effects at play in this process. It provides a practical route to various 1-C-diethylphosphono(difluoromethyl) iminosugars as glycosyl phosphate and sugar nucleotide mimics.

References

YearCitations

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