Literature DB >> 27185584

From glycals to aminosugars: a challenging test for new stereoselective aminohydroxylation and related methodologies.

S Mirabella1, F Cardona, A Goti.   

Abstract

The introduction of amino functionalities in a regio- and stereoselective manner onto sugar scaffolds represents a great challenge in carbohydrate synthesis. The most relevant methods to access 1-, 2-, 3-amino or 1,2-diaminosugars starting from glycals and 2,3-hexenopyranosides derived from them are concisely reviewed. The main synthetic strategies for accessing this class of compounds are classified in intermolecular and intramolecular approaches and the key features of each class are discussed. This review highlights how carbohydrate derivatives always pose great challenges representing a benchmark for assessing the efficiency of stereoselective strategies, and aims to give the readers inspiration for the development of new procedures.

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Year:  2016        PMID: 27185584     DOI: 10.1039/c6ob00649c

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  3 in total

1.  Glycal Metallanitrenes for 2-Amino Sugar Synthesis: Amidoglycosylation of Gulal-, Allal-, Glucal-, and Galactal 3-Carbamates.

Authors:  Simran Buttar; Julia Caine; Evelyne Goné; Reneé Harris; Jennifer Gillman; Roxanne Atienza; Ritu Gupta; Kimberly M Sogi; Lauren Jain; Nadia C Abascal; Yetta Levine; Lindsay M Repka; Christian M Rojas
Journal:  J Org Chem       Date:  2018-07-06       Impact factor: 4.354

2.  A stereoselective and flexible synthesis to access both enantiomers of N-acetylgalactosamine and peracetylated N-acetylidosamine.

Authors:  Bettina Riedl; Walther Schmid
Journal:  Beilstein J Org Chem       Date:  2018-04-13       Impact factor: 2.883

3.  Allyl Cyanate/Isocyanate Rearrangement in Glycals: Stereoselective Synthesis of 1-Amino and Diamino Sugar Derivatives.

Authors:  Stefania Mirabella; Giulia Petrucci; Cristina Faggi; Camilla Matassini; Francesca Cardona; Andrea Goti
Journal:  Org Lett       Date:  2020-11-04       Impact factor: 6.005

  3 in total

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