Literature DB >> 23780519

Catalytic regioselective oxidation of glycosides.

Manuel Jäger1, Marcel Hartmann, Johannes G de Vries, Adriaan J Minnaard.   

Abstract

Discrimination among equals: A catalytic method for the selective oxidation of unprotected glycosides, both monosaccharides and disaccharides, has been developed. The resulting ketosaccharides are isolated in moderate to excellent yields. This approach provides a basis for protecting-group-free synthetic transformations of carbohydrates.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbohydrates; glycosides; oxidation; palladium; regioselectivity

Year:  2013        PMID： 23780519     DOI： 10.1002/anie.201301662

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  9 in total

1.  Functional Characterization of the ycjQRS Gene Cluster from Escherichia coli: A Novel Pathway for the Transformation of d-Gulosides to d-Glucosides.

Authors:  Keya Mukherjee; Jamison P Huddleston; Tamari Narindoshvili; Venkatesh V Nemmara; Frank M Raushel
Journal:  Biochemistry       Date:  2019-02-20       Impact factor: 3.162

2.  Structure and Reaction Mechanism of YcjR, an Epimerase That Facilitates the Interconversion of d-Gulosides to d-Glucosides in Escherichia coli.

Authors:  Mark F Mabanglo; Jamison P Huddleston; Keya Mukherjee; Zane W Taylor; Frank M Raushel
Journal:  Biochemistry       Date:  2020-05-28       Impact factor: 3.162

3.  Regioselective Carbohydrate Oxidations: A Nuclear Magnetic Resonance (NMR) Study on Selectivity, Rate, and Side-Product Formation.

Authors:  Niek N H M Eisink; Martin D Witte; Adriaan J Minnaard
Journal:  ACS Catal       Date:  2017-01-18       Impact factor: 13.084

4.  β-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp)-H bonds using a palladium catalyst.

Authors:  Jing Peng; Chao Chen; Chanjuan Xi
Journal:  Chem Sci       Date:  2015-11-11       Impact factor: 9.825

5.  Selective Modification of Streptozotocin at the C3 Position to Improve Its Bioactivity as Antibiotic and Reduce Its Cytotoxicity towards Insulin-Producing β Cells.

Authors:  Ji Zhang; Liubov Yakovlieva; Bart J de Haan; Paul de Vos; Adriaan J Minnaard; Martin D Witte; Marthe T C Walvoort
Journal:  Antibiotics (Basel)       Date:  2020-04-15

6.  Late-Stage Modification of Aminoglycoside Antibiotics Overcomes Bacterial Resistance Mediated by APH(3') Kinases.

Authors:  Andreas A Bastian; Maria Bastian; Manuel Jäger; Mark Loznik; Eliza M Warszawik; Xintong Yang; Nabil Tahiri; Peter Fodran; Martin D Witte; Anne Thoma; Jens Köhler; Adriaan J Minnaard; Andreas Herrmann
Journal:  Chemistry       Date:  2022-05-17       Impact factor: 5.020

7.  Site-Selective Dehydroxy-Chlorination of Secondary Alcohols in Unprotected Glycosides.

Authors:  Ji Zhang; Niels R M Reintjens; Jayaraman Dhineshkumar; Martin D Witte; Adriaan J Minnaard
Journal:  Org Lett       Date:  2022-07-17       Impact factor: 6.072

Review 8.  Site-Selective Modification of (Oligo)Saccharides.

Authors:  Martin D Witte; Adriaan J Minnaard
Journal:  ACS Catal       Date:  2022-09-23       Impact factor: 13.700

9.  A protecting group-free synthesis of the Colorado potato beetle pheromone.

Authors:  Zhongtao Wu; Manuel Jäger; Jeffrey Buter; Adriaan J Minnaard
Journal:  Beilstein J Org Chem       Date:  2013-11-06       Impact factor: 2.883
  9 in total

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