Literature DB >> 24151089

A streamlined strategy for aglycone assembly and glycosylation.

Katherine M Partridge1, Scott J Bader, Zachary A Buchan, Christopher E Taylor, John Montgomery.   

Abstract

Multipurpose sugars: Carbohydrate-derived silane reagents are utilized as the reductant for nickel-catalyzed aldehyde-alkyne reductive coupling reactions and as the glycosyl donor for subsequent intramolecular glycosylation. The approach enables the assembly of the carbon-carbon framework and stereochemical features of an aglycone while simultaneously establishing the site of glycosylation.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  glycosylation; multicomponent reactions; nickel; silicon; synthetic methods

Mesh：

Substances：

Year:  2013        PMID： 24151089      PMCID： PMC3867577          DOI： 10.1002/anie.201307680

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  13 in total

Review 1.  Intramolecular aglycon delivery.

Authors:  Ian Cumpstey
Journal:  Carbohydr Res       Date:  2008-04-29       Impact factor: 2.104

2.  Nickel-Catalyzed Regiodivergent Approach to Macrolide Motifs.

Authors:  Abdur-Rafay Shareef; David H Sherman; John Montgomery
Journal:  Chem Sci       Date:  2011-12-06       Impact factor: 9.825

3.  A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes.

Authors:  Hasnain A Malik; Grant J Sormunen; John Montgomery
Journal:  J Am Chem Soc       Date:  2010-05-12       Impact factor: 15.419

Review 4.  Glycosyl fluorides in glycosidations.

Authors:  K Toshima
Journal:  Carbohydr Res       Date:  2000-07-10       Impact factor: 2.104

5.  New principles for glycoside-bond formation.

Authors:  Xiangming Zhu; Richard R Schmidt
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 6.  Thioglycosides in sequential glycosylation strategies.

Authors:  Jeroen D C Codée; Remy E J N Litjens; Leendert J van den Bos; Herman S Overkleeft; Gijsbert A van der Marel
Journal:  Chem Soc Rev       Date:  2005-07-27       Impact factor: 54.564

Review 7.  Nickel-catalyzed reductive cyclizations and couplings.

Authors:  John Montgomery
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-26       Impact factor: 15.336

8.  Ketone hydrosilylation with sugar silanes followed by intramolecular aglycone delivery: an orthogonal glycosylation strategy.

Authors:  Zachary A Buchan; Scott J Bader; John Montgomery
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Mechanism and transition-state structures for nickel-catalyzed reductive alkyne-aldehyde coupling reactions.

Authors:  P R McCarren; Peng Liu; Paul Ha-Yeon Cheong; Timothy F Jamison; K N Houk
Journal:  J Am Chem Soc       Date:  2009-05-20       Impact factor: 15.419

10.  Dehydrogenative cyclocondensation of aldehydes, alkynes, and dialkylsilanes.

Authors:  Ryan D Baxter; John Montgomery
Journal:  J Am Chem Soc       Date:  2008-07-04       Impact factor: 15.419
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  4 in total

1.  Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine.

Authors:  Guillaume Pelletier; Aaron Zwicker; C Liana Allen; Alanna Schepartz; Scott J Miller
Journal:  J Am Chem Soc       Date:  2016-03-01       Impact factor: 15.419

Review 2.  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

3.  Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation.

Authors:  Girish C Sati; Joshua L Martin; Yishu Xu; Tanmay Malakar; Paul M Zimmerman; John Montgomery
Journal:  J Am Chem Soc       Date:  2020-04-01       Impact factor: 15.419

4.  Sugar Silanes: Versatile Reagents for Stereocontrolled Glycosylation via Intramolecular Aglycone Delivery.

Authors:  Jordan T Walk; Zachary A Buchan; John Montgomery
Journal:  Chem Sci       Date:  2015-06-01       Impact factor: 9.825
  4 in total

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