4.5 Article

Application of the 2-Nitrobenzyl Group in Glycosylation Reactions: A Valuable Example of an Arming Participating Group

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 19, Pages 3988-3991

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300123

Keywords

Carbohydrates; Glycosylation; Protecting groups; Stereoselectivity

Funding

  1. EU European Regional Development Fund
  2. Polish National Science Centre [2012/05/B/ST5/0027]

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The application of the o-nitrobenzyl (oNBn) group is demonstrated. This practical methodology allows the stereocontrolled synthesis of glucosides with a 1,2-trans linkage. This new ether-type arming group can broadly extend the concept of the use of participating groups in glycosylation reactions. Easy protection and deprotection of the oNBn group further confirms its usefulness in synthesis.

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