Literature DB >> 18811175

A convenient Negishi protocol for the synthesis of glycosylated oligo(ethynylene)s.

Tobias N Hoheisel1, Holger Frauenrath.   

Abstract

A convenient and efficient sp-sp carbon heterocoupling protocol based on the Negishi reaction was developed, in which the required zinc diacetylide was generated from 1,4-bis(trimethylsilyl)butadiyne in situ and reacted with a bromoacetylene in apolar solvent mixtures. The method has been applied to the synthesis of unsymmetric glycosylated and symmetric diglycosylated oligo(ethynylene)s up to the octa(ethynylene).

Entities:  

Year:  2008        PMID： 18811175     DOI： 10.1021/ol801807a

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


  8 in total

1.  Intermediates and Reactivity in Iron-Catalyzed Cross-Couplings of Alkynyl Grignards with Alkyl Halides.

Authors:  Jared L Kneebone; William W Brennessel; Michael L Neidig
Journal:  J Am Chem Soc       Date:  2017-05-16       Impact factor: 15.419

2.  Synthesis of saccharin-glycoconjugates targeting carbonic anhydrase using a one-pot cyclization/deprotection strategy.

Authors:  Akilah B Murray; Marta Quadri; Haoxi Li; Robert McKenna; Nicole A Horenstein
Journal:  Carbohydr Res       Date:  2019-03-19       Impact factor: 2.104

3.  Functional carbon nanosheets prepared from hexayne amphiphile monolayers at room temperature.

Authors:  Stephen Schrettl; Cristina Stefaniu; Christian Schwieger; Guillaume Pasche; Emad Oveisi; Yannik Fontana; Anna Fontcuberta i Morral; Javier Reguera; Riccardo Petraglia; Clémence Corminboeuf; Gerald Brezesinski; Holger Frauenrath
Journal:  Nat Chem       Date:  2014-05-04       Impact factor: 24.427

4.  Facile synthesis of oligoyne amphiphiles and their rotaxanes.

Authors:  Stephen Schrettl; Emmanuel Contal; Tobias N Hoheisel; Martin Fritzsche; Sandor Balog; Ruth Szilluweit; Holger Frauenrath
Journal:  Chem Sci       Date:  2014-10-24       Impact factor: 9.825

5.  Preparation of Carbon Nanosheets at Room Temperature.

Authors:  Stephen Schrettl; Bjoern Schulte; Cristina Stefaniu; Joana Oliveira; Gerald Brezesinski; Holger Frauenrath
Journal:  J Vis Exp       Date:  2016-03-08       Impact factor: 1.355

6.  A multistep single-crystal-to-single-crystal bromodiacetylene dimerization.

Authors:  Tobias N Hoheisel; Stephen Schrettl; Roman Marty; Tanya K Todorova; Clémence Corminboeuf; Andrzej Sienkiewicz; Rosario Scopelliti; W Bernd Schweizer; Holger Frauenrath
Journal:  Nat Chem       Date:  2013-02-24       Impact factor: 24.427

7.  Quantitative Structure-Retention Relationships for Polycyclic Aromatic Hydrocarbons and their Oligoalkynyl-Substituted Derivatives.

Authors:  Gaël Rouillé; Cornelia Jäger; Friedrich Huisken; Thomas Henning; Regina Czerwonka; Gabriele Theumer; Carsten Börger; Ingmar Bauer; Hans-Joachim Knölker
Journal:  ChemistryOpen       Date:  2017-07-13       Impact factor: 2.911

8.  Unified total synthesis of the natural products endiandric acid A, kingianic acid E, and kingianins A, D, and F.

Authors:  S L Drew; A L Lawrence; M S Sherburn
Journal:  Chem Sci       Date:  2015-05-07       Impact factor: 9.825
  8 in total

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