Literature DB >> 12599507

Stereoselective synthesis of L-oliose trisaccharide via iterative alkynol cycloisomerization and acid-catalyzed glycosylation.

Frank E McDonald1, Minglang Wu.   

Abstract

[formula: see text] The synthesis of an all-alpha L-oliose diastereomer of digitoxin provides valuable insights into the generality and protective-group dependence of acid-catalyzed glycosylations of glycals to 2-deoxycarbohydrates.

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Year:  2002        PMID： 12599507     DOI： 10.1021/ol026886o

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

Review 1.  Methods for 2-Deoxyglycoside Synthesis.

Authors:  Clay S Bennett; M Carmen Galan
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

2.  A stereoselective synthesis of digitoxin and digitoxigen mono- and bisdigitoxoside from digitoxigenin via a palladium-catalyzed glycosylation.

Authors:  Maoquan Zhou; George A O'Doherty
Journal:  Org Lett       Date:  2006-09-14       Impact factor: 6.005

3.  Fischer carbene catalysis of alkynol cycloisomerization: application to the synthesis of the altromycin B disaccharide.

Authors:  Bonsuk Koo; Frank E McDonald
Journal:  Org Lett       Date:  2007-03-27       Impact factor: 6.005

4.  De novo approach to 2-deoxy-beta-glycosides: asymmetric syntheses of digoxose and digitoxin.

Authors:  Maoquan Zhou; George A O'Doherty
Journal:  J Org Chem       Date:  2007-03-06       Impact factor: 4.354

5.  Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks.

Authors:  Subbarao Yalamanchili; Tu-Anh Nguyen; Alexander Zsikla; Gavin Stamper; Ashley E DeYong; John Florek; Olivea Vasquez; Nicola L B Pohl; Clay S Bennett
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-21       Impact factor: 16.823

6.  Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals.

Authors:  Subbarao Yalamanchili; Tu-Anh V Nguyen; Nicola L B Pohl; Clay S Bennett
Journal:  Org Biomol Chem       Date:  2020-05-06       Impact factor: 3.876

7.  Brønsted acid-promoted glycosylations of disaccharide glycal substructures of the saccharomicins.

Authors:  Bradley R Balthaser; Frank E McDonald
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

8.  Rapid de Novo Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization.

Authors:  Subbarao Yalamanchili; William Miller; Xizhao Chen; Clay S Bennett
Journal:  Org Lett       Date:  2019-11-22       Impact factor: 6.005
  8 in total

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