Literature DB >> 31534883

Recent Developments in Stereoselective Chemical Glycosylation.

Jesse Ling1, Clay S Bennett1.   

Abstract

Because of their pivotal biological functions, attention to sugars and glycobiology has grown rapidly in recent decades, leading to increased demand for homogeneous oligosaccharides. The stereoselective preparation of oligosaccharides by chemical means remains challenging and continues to be a vivid research area for organic chemists. In the past decade, new approaches and reinvestigated traditional methods have transformed the field. These developments include novel catalyses, various types of glycosylation modulators and the use of photochemical energy to facilitate glycosylation. This Minireview presents a brief overview of the latest trends in chemical glycosylation, with emphasis on the stereoselective synthetic protocols developed in the past decade.

Entities:  

Keywords:  carbohydrates; diastereoselectivity; glycosides; glycosylation; oligosaccharides

Year:  2019        PMID: 31534883      PMCID: PMC6750748          DOI: 10.1002/ajoc.201900102

Source DB:  PubMed          Journal:  Asian J Org Chem        ISSN: 2193-5807            Impact factor:   3.319


  73 in total

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Authors:  Raymond A. Dwek
Journal:  Chem Rev       Date:  1996-03-28       Impact factor: 60.622

2.  Formation of beta-Mannopyranosides of Primary Alcohols Using the Sulfoxide Method.

Authors:  David Crich; Sanxing Sun
Journal:  J Org Chem       Date:  1996-07-12       Impact factor: 4.354

3.  Sulfoxide covalent catalysis: application to glycosidic bond formation.

Authors:  Timothy A Boebel; David Y Gin
Journal:  Angew Chem Int Ed Engl       Date:  2003       Impact factor: 15.336

Review 4.  Reaction progress kinetic analysis: a powerful methodology for mechanistic studies of complex catalytic reactions.

Authors:  Donna G Blackmond
Journal:  Angew Chem Int Ed Engl       Date:  2005-07-11       Impact factor: 15.336

5.  Gold mediated glycosylations: selective activation of propargyl 1,2-orthoesters in the presence of aglycones containing a propargyl moiety.

Authors:  Gopalsamy Sureshkumar; Srinivas Hotha
Journal:  Chem Commun (Camb)       Date:  2008-07-21       Impact factor: 6.222

6.  Probing the mechanism of sulfoxide-catalyzed hemiacetal activation in dehydrative glycosylation.

Authors:  Timothy A Boebel; David Y Gin
Journal:  J Org Chem       Date:  2005-07-22       Impact factor: 4.354

7.  1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.

Authors:  D Crich; M Smith
Journal:  J Am Chem Soc       Date:  2001-09-19       Impact factor: 15.419

8.  Propargyl glycosides as stable glycosyl donors: anomeric activation and glycoside syntheses.

Authors:  Srinivas Hotha; Sudhir Kashyap
Journal:  J Am Chem Soc       Date:  2006-08-02       Impact factor: 15.419

9.  Mechanism of 4,6-O-benzylidene-directed beta-mannosylation as determined by alpha-deuterium kinetic isotope effects.

Authors:  David Crich; N Susantha Chandrasekera
Journal:  Angew Chem Int Ed Engl       Date:  2004-10-11       Impact factor: 15.336

10.  Palladium-controlled beta-selective glycosylation in the absence of the C(2)-ester participatory group.

Authors:  Enoch A Mensah; Joseph M Azzarelli; Hien M Nguyen
Journal:  J Org Chem       Date:  2009-02-20       Impact factor: 4.354

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  6 in total

1.  Mimicry of the proton wire mechanism of enzymes inside a supramolecular capsule enables β-selective O-glycosylations.

Authors:  Tian-Ren Li; Fabian Huck; GiovanniMaria Piccini; Konrad Tiefenbacher
Journal:  Nat Chem       Date:  2022-07-07       Impact factor: 24.274

Review 2.  Recent Advances in Stereoselective Chemical O-Glycosylation Reactions.

Authors:  Mana Mohan Mukherjee; Rina Ghosh; John A Hanover
Journal:  Front Mol Biosci       Date:  2022-06-14

3.  Streamlined Iterative Assembly of Thio-Oligosaccharides by Aqueous S-Glycosylation of Diverse Deoxythio Sugars.

Authors:  Peng Wen; Peijing Jia; Qiuhua Fan; Bethany J McCarty; Weiping Tang
Journal:  ChemSusChem       Date:  2022-01-10       Impact factor: 9.140

4.  Hydrogen bond activated glycosylation under mild conditions.

Authors:  Ke Xiao; Yongxin Hu; Yongyong Wan; XinXin Li; Qin Nie; Hao Yan; Liming Wang; Jinxi Liao; Deyong Liu; Yuanhong Tu; Jiansong Sun; Jeroen D C Codée; Qingju Zhang
Journal:  Chem Sci       Date:  2021-12-15       Impact factor: 9.825

5.  AuCl3-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives.

Authors:  Robin Jeanneret; Carlo Walz; Maarten van Meerbeek; Sarah Coppock; M Carmen Galan
Journal:  Org Lett       Date:  2022-08-22       Impact factor: 6.072

6.  Synthetic Carbohydrate Chemistry and Translational Medicine.

Authors:  Sachin S Shivatare; Chi-Huey Wong
Journal:  J Org Chem       Date:  2020-10-30       Impact factor: 4.354

  6 in total

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