Literature DB >> 26294060

Selective Protection of Secondary Amines as the N-Phenyltriazenes. Application to Aminoglycoside Antibiotics.

Amr Sonousi1, David Crich1.   

Abstract

Selective protection of secondary amines as triazenes in the presence of multiple primary amines is demonstrated, with subsequent protection of the primary amines as either azides or carbamates in the same pot. Aminoglycoside antibiotic examples reveal broad functional group compatibility. The triazene group is removed with trifluoroacetic acid and, because of the low barrier to rotation, affords sharp (1)H NMR spectra at room temperature.

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Year:  2015        PMID： 26294060      PMCID： PMC4547389          DOI： 10.1021/acs.orglett.5b01902

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


  15 in total

1.  The First Stable Diazonium Ion on Solid Support-Investigations on Stability and Usage as Linker and Scavenger in Solid-Phase Organic Synthesis Nitrogen-Based Linkers, Part 8. This work was supported by the Fonds der Chemischen Industrie (Liebig-Stipend to S.B.) and the Deutsche Forschungsgemeinschaft (BR1750-1). We thank Prof. Dr. D. Enders for the generous support of our work. The companies BASF AG, Bayer AG, Degussa-Hüls AG, and Calbiochem-Novabiochem AG are acknowledged for donations of chemicals and Grünenthal GmbH for financial support. For DSC measurements we also thank Prof. Dr. Franz-Josef Wortmann and Dr. Numan Özgün at the Deutsches Wollforschungsinstitut (DWI) at the RWTH Aachen. Part 7: M. Lormann, S. Dahmen, S. Bräse, Tetrahedron Lett. 2000, 41, 3813-3816.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-10-16       Impact factor: 15.336

2.  Synthesis of aryl fluorides on a solid support and in solution by utilizing a fluorinated solvent.

Authors:  Marion Döbele; Sylvia Vanderheiden; Nicole Jung; Stefan Bräse
Journal:  Angew Chem Int Ed Engl       Date:  2010-08-09       Impact factor: 15.336

3.  Sensitivities of some imidazole-1-sulfonyl azide salts.

Authors:  Niko Fischer; Ethan D Goddard-Borger; Robert Greiner; Thomas M Klapötke; Brian W Skelton; Jörg Stierstorfer
Journal:  J Org Chem       Date:  2012-02-09       Impact factor: 4.354

4.  A safe and facile route to imidazole-1-sulfonyl azide as a diazotransfer reagent.

Authors:  Hui Ye; Ruihua Liu; Dongmei Li; Yonghui Liu; Haixin Yuan; Weikang Guo; Lifei Zhou; Xuefeng Cao; Hongqi Tian; Jie Shen; Peng George Wang
Journal:  Org Lett       Date:  2012-12-14       Impact factor: 6.005

Review 5.  Structures and syntheses of aminoglycoside antibiotics.

Authors:  S Umezawa
Journal:  Adv Carbohydr Chem Biochem       Date:  1974       Impact factor: 12.200

Review 6.  Triazenes: a versatile tool in organic synthesis.

Authors:  David B Kimball; Michael M Haley
Journal:  Angew Chem Int Ed Engl       Date:  2002-09-16       Impact factor: 15.336

7.  Triazene as a powerful tool for solid-phase derivatization of phenylalanine containing peptides: zygosporamide analogues as a proof of concept.

Authors:  Carolina Torres-García; Daniel Pulido; Fernando Albericio; Miriam Royo; Ernesto Nicolás
Journal:  J Org Chem       Date:  2014-11-18       Impact factor: 4.354

8.  A novel solid-phase synthesis of highly diverse guanidines: reactions of primary amines attached to the T2 linker.

Authors:  S Dahmen; S Bräse
Journal:  Org Lett       Date:  2000-11-16       Impact factor: 6.005

Review 9.  The virtue of the multifunctional triazene linkers in the efficient solid-phase synthesis of heterocycle libraries.

Authors:  Stefan Bräse
Journal:  Acc Chem Res       Date:  2004-10       Impact factor: 22.384

10.  An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride.

Authors:  Ethan D Goddard-Borger; Robert V Stick
Journal:  Org Lett       Date:  2007-08-22       Impact factor: 6.005
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  3 in total

1.  Effects of the 1- N-(4-Amino-2 S-hydroxybutyryl) and 6'- N-(2-Hydroxyethyl) Substituents on Ribosomal Selectivity, Cochleotoxicity, and Antibacterial Activity in the Sisomicin Class of Aminoglycoside Antibiotics.

Authors:  Amr Sonousi; Vikram A Sarpe; Margarita Brilkova; Jochen Schacht; Andrea Vasella; Erik C Böttger; David Crich
Journal:  ACS Infect Dis       Date:  2018-05-10       Impact factor: 5.084

2.  Synthesis, ribosomal selectivity, and antibacterial activity of netilmicin 4'-derivatives.

Authors:  Amr Sonousi; Dimitri Shcherbakov; Andrea Vasella; Erik C Böttger; David Crich
Journal:  Medchemcomm       Date:  2019-04-25       Impact factor: 3.597

Review 3.  Covalent Chemical Tools for Profiling Post-Translational Modifications.

Authors:  Benjamin Emenike; Ogonna Nwajiobi; Monika Raj
Journal:  Front Chem       Date:  2022-07-04       Impact factor: 5.545
  3 in total

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