Literature DB >> 25862946

Common side reactions of the glycosyl donor in chemical glycosylation.

Helle M Christensen1, Stefan Oscarson2, Henrik H Jensen3.   

Abstract

Chemical glycosylation is central to carbohydrate chemistry and is generally recognised as a challenging reaction. This review describes the most reoccurring side reactions of glycosyl donors in glycosylation and how scientists have attempted to explain their observations and in some cases succeeded in solving a particular encountered problem. The topics covered are donor hydrolysis, elimination to form glycals, intermolecular aglycon transfer of thioglycosides and glycosyl imidate rearrangement.
Copyright © 2015 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  By-products; Elimination; Hydrolysis; Thioglycosides; Trichloroacetimidates

Mesh：

Substances：

Year:  2015        PMID： 25862946     DOI： 10.1016/j.carres.2015.02.007

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN： 0008-6215            Impact factor:   2.104


  19 in total

1.  Synthesis of an Aminooxy Derivative of the GM3 Antigen and Its Application in Oxime Ligation.

Authors:  Kristopher A Kleski; Mengchao Shi; Matthew Lohman; Gabrielle T Hymel; Vinod K Gattoji; Peter R Andreana
Journal:  J Org Chem       Date:  2020-05-01       Impact factor: 4.354

2.  Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.

Authors:  Asiri A Hettikankanamalage; Robert Lassfolk; Filip S Ekholm; Reko Leino; David Crich
Journal:  Chem Rev       Date:  2020-07-05       Impact factor: 60.622

3.  Catalytic activation of glycosyl phosphates for stereoselective coupling reactions.

Authors:  Samuel M Levi; Qiuhan Li; Andreas R Rötheli; Eric N Jacobsen
Journal:  Proc Natl Acad Sci U S A       Date:  2018-12-17       Impact factor: 11.205

4.  Further studies on cation clock reactions in glycosylation: observation of a configuration specific intramolecular sulfenyl transfer and isolation and characterization of a tricyclic acetal.

Authors:  Min Huang; Takayuki Furukawa; Pascal Retailleau; David Crich; Luis Bohé
Journal:  Carbohydr Res       Date:  2016-04-06       Impact factor: 2.104

5.  Rearrangement of Benzylic Trichloroacetimidates to Benzylic Trichloroacetamides.

Authors:  Arijit A Adhikari; Tamie Suzuki; Reesheda T Gilbert; Matthew R Linaburg; John D Chisholm
Journal:  J Org Chem       Date:  2017-03-27       Impact factor: 4.354

6.  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

Review 7.  Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

Authors:  Yashapal Singh; Scott A Geringer; Alexei V Demchenko
Journal:  Chem Rev       Date:  2022-06-08       Impact factor: 72.087

8.  HPLC-Assisted Automated Oligosaccharide Synthesis: Implementation of the Autosampler as a Mode of the Reagent Delivery.

Authors:  Salvatore G Pistorio; Swati S Nigudkar; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2016-09-14       Impact factor: 4.354

9.  Synthesis of 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-manno derivatives as versatile building blocks.

Authors:  Catherine Alex; Satsawat Visansirikul; Yongzhen Zhang; Jagodige P Yasomanee; Jeroen Codee; Alexei V Demchenko
Journal:  Carbohydr Res       Date:  2019-12-23       Impact factor: 2.104

10.  Influence of Configuration at the 4- and 6-Positions on the Conformation and Anomeric Reactivity and Selectivity of 7-Deoxyheptopyranosyl Donors: Discovery of a Highly Equatorially Selective l-glycero-d-gluco-Heptopyranosyl Donor.

Authors:  Kapil Upadhyaya; Rahul S Bagul; David Crich
Journal:  J Org Chem       Date:  2021-08-03       Impact factor: 4.198
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.