Literature DB >> 31613104

Dual-Participation Protecting Group Solves the Anomeric Stereocontrol Problems in Glycosylation Reactions.

Hui Liu1, Thomas Hansen2, Si-Yu Zhou1, Guo-En Wen1, Xu-Xue Liu1, Qing-Ju Zhang1, Jeroen D C Codée2, Richard R Schmidt1,3, Jian-Song Sun1.   

Abstract

The 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) group permits, via robust neighboring group participation (NGP) or long distance participation (LDP) effects, the stereocontrolled 1,2-trans, 1,2-cis, as well as β-2,6-dideoxy glycosidic bond generation, while suppressing the undesired orthoester byproduct formation. The robust stereocontrol capability of the DMNPA is due to the dual-participation effect from both the ester functionality and the nitro group, verified by control reactions and DFT calculations and further corroborated by X-ray spectroscopy.

Entities:  

Year:  2019        PMID： 31613104     DOI： 10.1021/acs.orglett.9b03321

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

2.  Stabilization of Glucosyl Dioxolenium Ions by "Dual Participation" of the 2,2-Dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) Protection Group for 1,2-cis-Glucosylation.

Authors:  Wouter A Remmerswaal; Kas J Houthuijs; Roel van de Ven; Hidde Elferink; Thomas Hansen; Giel Berden; Herman S Overkleeft; Gijsbert A van der Marel; Floris P J T Rutjes; Dmitri V Filippov; Thomas J Boltje; Jonathan Martens; Jos Oomens; Jeroen D C Codée
Journal:  J Org Chem       Date:  2022-06-24       Impact factor: 4.198

3.  Stereocontrolled α-Galactosylation under Cooperative Catalysis.

Authors:  Melanie Shadrick; Yashapal Singh; Alexei V Demchenko
Journal:  J Org Chem       Date:  2020-10-16       Impact factor: 4.354

4.  Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions.

Authors:  Thomas Hansen; Hidde Elferink; Jacob M A van Hengst; Kas J Houthuijs; Wouter A Remmerswaal; Alexandra Kromm; Giel Berden; Stefan van der Vorm; Anouk M Rijs; Hermen S Overkleeft; Dmitri V Filippov; Floris P J T Rutjes; Gijsbert A van der Marel; Jonathan Martens; Jos Oomens; Jeroen D C Codée; Thomas J Boltje
Journal:  Nat Commun       Date:  2020-05-29       Impact factor: 14.919

5.  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

6.  Protecting group free glycosylation: one-pot stereocontrolled access to 1,2-trans glycosides and (1→6)-linked disaccharides of 2-acetamido sugars.

Authors:  Xin Qiu; Anna L Garden; Antony J Fairbanks
Journal:  Chem Sci       Date:  2022-03-17       Impact factor: 9.825

Review 7.  Recent advances in stereoselective 1,2-cis-O-glycosylations.

Authors:  Akihiro Ishiwata; Katsunori Tanaka; Jiaming Ao; Feiqing Ding; Yukishige Ito
Journal:  Front Chem       Date:  2022-08-19       Impact factor: 5.545

8.  Reactivity-Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides.

Authors:  Thomas Hansen; Tim P Ofman; Joey G C Vlaming; Ivan A Gagarinov; Jessey van Beek; Tessa A Goté; Jacoba M Tichem; Gijs Ruijgrok; Herman S Overkleeft; Dmitri V Filippov; Gijsbert A van der Marel; Jeroen D C Codée
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-03       Impact factor: 16.823
  8 in total

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