Literature DB >> 35675037

Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

Yashapal Singh1, Scott A Geringer1, Alexei V Demchenko1,2.   

Abstract

Advances in synthetic carbohydrate chemistry have dramatically improved access to common glycans. However, many novel methods still fail to adequately address challenges associated with chemical glycosylation and glycan synthesis. Since a challenge of glycosylation has remained, scientists have been frequently returning to the traditional glycosyl donors. This review is dedicated to glycosyl halides that have played crucial roles in shaping the field of glycosciences and continue to pave the way toward our understanding of chemical glycosylation.

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Year:  2022        PMID: 35675037      PMCID: PMC9417321          DOI: 10.1021/acs.chemrev.2c00029

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   72.087


  274 in total

1.  Stereospecific 1,2-cis-glycosylation: a modified thiocyanate method.

Authors:  N K Kochetkov; E M Klimov; N N Malysheva; A V Demchenko
Journal:  Carbohydr Res       Date:  1992-07-20       Impact factor: 2.104

Review 2.  Glycoprotein synthesis: an update.

Authors:  David P Gamblin; Eoin M Scanlan; Benjamin G Davis
Journal:  Chem Rev       Date:  2009-01       Impact factor: 60.622

3.  One-pot syntheses of immunostimulatory glycolipids.

Authors:  Matthew Schombs; Francine E Park; Wenjun Du; Suvarn S Kulkarni; Jacquelyn Gervay-Hague
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

4.  A new C(1)-auxiliary for anomeric stereocontrol in the synthesis of alpha-sialyl glycosides.

Authors:  J M Haberman; D Y Gin
Journal:  Org Lett       Date:  2001-05-31       Impact factor: 6.005

Review 5.  Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation.

Authors:  Sophon Kaeothip; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2011-05-18       Impact factor: 2.104

6.  Direct dehydrative pyridylthio-glycosidation of unprotected sugars in aqueous media using 2-chloro-1,3-dimethylimidazolinium chloride as a condensing agent.

Authors:  Naoki Yoshida; Masato Noguchi; Tomonari Tanaka; Takeshi Matsumoto; Naoya Aida; Masaki Ishihara; Atsushi Kobayashi; Shin-ichiro Shoda
Journal:  Chem Asian J       Date:  2011-05-23

7.  A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions.

Authors:  Peter H Huy; Isabel Filbrich
Journal:  Chemistry       Date:  2018-04-26       Impact factor: 5.236

8.  Automated Solution-Phase Synthesis of S-Glycosides for the Production of Oligomannopyranoside Derivatives.

Authors:  Mallory K Kern; Nicola L B Pohl
Journal:  Org Lett       Date:  2020-05-20       Impact factor: 6.005

9.  α-Selective organocatalytic synthesis of 2-deoxygalactosides.

Authors:  Edward I Balmond; Diane M Coe; M Carmen Galan; Eoghan M McGarrigle
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-09       Impact factor: 15.336

10.  Glycosidic bond formation in aqueous solution: on the oxocarbenium intermediate.

Authors:  John M Stubbs; Dominik Marx
Journal:  J Am Chem Soc       Date:  2003-09-10       Impact factor: 15.419

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