Literature DB >> 30286335

Investigation of the H-bond-mediated aglycone delivery reaction in application to the synthesis of β-glucosides.

Michael P Mannino1, Jagodige P Yasomanee1, Alexei V Demchenko2.   

Abstract

In an attempt to refine the H-bond-mediated Aglycone Delivery (HAD) glycosylation reaction reported herein is the synthesis of β-glucosides using an ethylthio glucoside donor equipped with the remote 6-O-picoloyl substituent. Upon examining various aliphatic, aromatic, and carbohydrate acceptors, it was determined that both electronic and steric factors may greatly affect the stereoselectivity of the HAD reaction with this donor.
Copyright © 2018 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Glycosylation; Oligosaccharides; Stereoselectivity; Synthesis

Mesh:

Substances:

Year:  2018        PMID: 30286335      PMCID: PMC6215728          DOI: 10.1016/j.carres.2018.09.003

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


  21 in total

1.  2,3-Di-O-picolinyl building blocks as glycosyl donors with switchable stereoselectivity.

Authors:  Jagodige P Yasomanee; Archana R Parameswar; Papapida Pornsuriyasak; Nigam P Rath; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2016-02-25       Impact factor: 3.876

Review 2.  Neighboring-group participation in sugars.

Authors:  L Goodman
Journal:  Adv Carbohydr Chem Biochem       Date:  1967       Impact factor: 12.200

3.  C6 picoloyl protection: a remote stereodirecting group for 2-deoxy-β-glycoside formation.

Authors:  Jyh-Herng Ruei; Patteti Venukumar; Arun B Ingle; Kwok-Kong Tony Mong
Journal:  Chem Commun (Camb)       Date:  2015-03-28       Impact factor: 6.222

4.  Combined Effect of the Picoloyl Protecting Group and Triflic Acid in Sialylation.

Authors:  Samira Escopy; Scott A Geringer; Cristina De Meo
Journal:  Org Lett       Date:  2017-04-28       Impact factor: 6.005

5.  β-Arabinofuranosylation using 5-O-(2-quinolinecarbonyl) substituted ethyl thioglycoside donors.

Authors:  Qiang-Wei Liu; Hua-Chao Bin; Jin-Song Yang
Journal:  Org Lett       Date:  2013-07-23       Impact factor: 6.005

6.  Synthesis and applications of a light-fluorous glycosyl donor.

Authors:  Fa Zhang; Wei Zhang; Yan Zhang; Dennis P Curran; Gang Liu
Journal:  J Org Chem       Date:  2009-03-20       Impact factor: 4.354

7.  Hydrogen-bond-mediated aglycone delivery: focus on β-mannosylation.

Authors:  Salvatore G Pistorio; Jagodige P Yasomanee; Alexei V Demchenko
Journal:  Org Lett       Date:  2014-01-28       Impact factor: 6.005

8.  6-O-Picolinyl and 6-O-Picoloyl Building Blocks As Glycosyl Donors with Switchable Stereoselectivity.

Authors:  Abhijeet K Kayastha; Xiao G Jia; Jagodige P Yasomanee; Alexei V Demchenko
Journal:  Org Lett       Date:  2015-09-09       Impact factor: 6.005

9.  Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry.

Authors:  Swati S Nigudkar; Alexei V Demchenko
Journal:  Chem Sci       Date:  2015-05-01       Impact factor: 9.825

Review 10.  Chemical O-Glycosylations: An Overview.

Authors:  Rituparna Das; Balaram Mukhopadhyay
Journal:  ChemistryOpen       Date:  2016-08-17       Impact factor: 2.911

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  1 in total

1.  Picoloyl protecting group in synthesis: focus on a highly chemoselective catalytic removal.

Authors:  Scott A Geringer; Michael P Mannino; Mithila D Bandara; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2020-07-01       Impact factor: 3.876

  1 in total

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