Literature DB >> 22007683

The influence of neighboring group participation on the hydrolysis of 2-O-substituted methyl glucopyranosides.

Mads Heuckendorff1, Christian M Pedersen, Mikael Bols.   

Abstract

Does neighboring group participation actually enhance the reactivity of the anomeric center when the participating group is inherently disarming? To investigate the influence of the neighboring group effect from a 2-O protective group on acidic glycoside hydrolysis, 10 methyl glucosides having different protective groups on O2 have been synthesized and a clear trend between anomeric configuration, participation of the protective group, and the rate of hydrolysis could be observed.

Entities:  

Year:  2011        PMID： 22007683     DOI： 10.1021/ol202308y

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


  8 in total

1.  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

Review 2.  The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Authors:  Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal:  Chem Rev       Date:  2018-05-30       Impact factor: 60.622

3.  Superarming of glycosyl donors by combined neighboring and conformational effects.

Authors:  Mads Heuckendorff; Hemali D Premathilake; Papapida Pornsuriyasak; Anders Ø Madsen; Christian M Pedersen; Mikael Bols; Alexei V Demchenko
Journal:  Org Lett       Date:  2013-09-05       Impact factor: 6.005

4.  Acceleration of acetal hydrolysis by remote alkoxy groups: evidence for electrostatic effects on the formation of oxocarbenium ions.

Authors:  Angie Garcia; Douglas A L Otte; Walter A Salamant; Jillian R Sanzone; K A Woerpel
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-22       Impact factor: 15.336

5.  Halogen Atom Participation in Guiding the Stereochemical Outcomes of Acetal Substitution Reactions.

Authors:  Krystyna M Demkiw; Wouter A Remmerswaal; Thomas Hansen; Gijsbert A van der Marel; Jeroen D C Codée; K A Woerpel
Journal:  Angew Chem Int Ed Engl       Date:  2022-09-16       Impact factor: 16.823

6.  Glycosyl Exchange of Unactivated Glycosidic Bonds: Suppressing or Embracing Side Reactivity in Catalytic Glycosylations.

Authors:  Joshua L Martin; Girish C Sati; Tanmay Malakar; Jessica Hatt; Paul M Zimmerman; John Montgomery
Journal:  J Org Chem       Date:  2022-04-12       Impact factor: 4.198

7.  Using Neighboring-Group Participation for Acyclic Stereocontrol in Diastereoselective Substitution Reactions of Acetals.

Authors:  Amanda Ramdular; K A Woerpel
Journal:  Org Lett       Date:  2020-05-11       Impact factor: 6.005

8.  Towards a Systematic Understanding of the Influence of Temperature on Glycosylation Reactions.

Authors:  Owen T Tuck; Eric T Sletten; José Danglad-Flores; Peter H Seeberger
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-15       Impact factor: 16.823
  8 in total

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