Literature DB >> 15149212

A new method for the stereoselective synthesis of alpha- and beta-glycosylamines using the Burgess reagent.

K C Nicolaou1, Scott A Snyder, Annie Z Nalbandian, Deborah A Longbottom.   

Abstract

Although glycosylamines constitute an important group of carbohydrates from the standpoint of biology and medicine, methods for their synthesis typically lack substrate generality and/or result in variable stereoselectivity, especially in complex contexts. In this communication, we report an operationally simple method for the synthesis of both alpha- and beta-glycosylamines using the Burgess reagent that overcomes many of these limitations in a bare minimum of synthetic steps.

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Year:  2004        PMID: 15149212     DOI: 10.1021/ja049293c

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  3 in total

Review 1.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

2.  A Solvent-free Approach to Glycosyl Amides: Towards the Synthesis of α-N-Galactosyl Ceramides.

Authors:  Divya Chennamadhavuni; Amy R Howell
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

3.  Self-promoted and stereospecific formation of N-glycosides.

Authors:  Michael Martin Nielsen; Patrycja Mała; Eirikur Þórir Baldursson; Christian Marcus Pedersen
Journal:  Chem Sci       Date:  2019-04-18       Impact factor: 9.825

  3 in total

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