A short route for the synthesis of “sweet” macrocycles via a click-dimerization–ring-closing metathesis approach

Dörner, Simon; Westermann, Bernhard

doi:10.1039/b502682b

Cited by 67 publications

(34 citation statements)

References 26 publications

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“…[31,32] The terminal C C triple bond can undergo 1,3-dipolar cycloaddition with azides under mild conditions and at a wide range of functional group compatibility. [33][34][35][36][37][38] In an interesting approach, biodegradable microcapsules have been produced by 'clicking together' acetylenic and azido derivatives of dextrans. [39] We now report on the preparation, substituent distribution studies, structure formation and metal complexation of alkynyldextrans.…”

Section: Introductionmentioning

confidence: 99%

Alkynyl Ethers of Glucans: Substituent Distribution in Propargyl‐, Pentynyl‐ and Hexynyldextrans and ‐amyloses and Support for Silver Nanoparticle Formation

Tahir

Bork

Risberg

et al. 2010

Macro Chemistry & Physics

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Alkynyldextrans with a DS in the range 0.1–1.67 have been prepared as reactive intermediates for further polymer‐analogous functionalisation. DS and substituent distribution were determined by GLC and GLCMS after hydrolysis and acetylation, or methanolysis and trimethylsilylation. Reactivity was in the order O‐2 > O‐4 ≥ O‐3 with pronounced differences in the distinct patterns for propargyl ethers and its higher homologous. A large deviation from a random substituent distribution was observed. Propargyldextrans were not stable during long‐time storage in the solid state, while terminal pentynyl and hexynyl ethers are. Pentynyldextrans showed structure formation of various geometries. They bound silver efficiently, yielding silver nanoparticles by reduction.magnified image

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Section: Introductionmentioning

confidence: 99%

Alkynyl Ethers of Glucans: Substituent Distribution in Propargyl‐, Pentynyl‐ and Hexynyldextrans and ‐amyloses and Support for Silver Nanoparticle Formation

Tahir

Bork

Risberg

et al. 2010

Macro Chemistry & Physics

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“…Dörner and Westermann [83] used this reaction to prepare macrocyclic natural product mimetics of cyclic glycolipids containing two triazoles for the linkage of the functional sugars. 6-Azidoglucopyranose derivatives containing lipid precursors for the RCM were linked together by bis-triazole formation with octadiyne Cu(I) prior to cyclization.…”

Section: General Considerations In Cuaac Click Chemistry In Polymer Smentioning

confidence: 99%

Polymer “Clicking” by CuAAC Reactions

Meldal

2008

Macromol. Rapid Commun.

330

151

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The CuAAC “click” reaction has developed as one of the most useful and widely employed reactions in ligation within polymer chemistry. This is due to the unique properties of the Cu(I) catalysis which renders the reaction quantitative even at low concentrations, orthogonal with other chemistries and extremely robust. The formed triazole on the other hand is of intermediate polarity and chemically and biochemically “invisible”, and the CuAAC provides the ideal “click” reaction for stitching together polymer architectures of unprecedended complexity as was it molecular LEGO. The CuAAC “clicking” in polymer chemistry is increasing exponentially and lead to highly defined polymer materials with novel properties.magnified image

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“…For the synthesis of sugar and thiazole containing macrocycles Westermann et al utilized [83] the RCM reaction. A facile and short route for the synthesis of sugar containing macrocycles (sweet macrocycles) via a click dimerization and ring closing metathesis approach was presented by Wastermann and co-workers.…”

Section: Synthesis Of Nitrogen Phosphorus and Sulphur Heterocyclesmentioning

confidence: 99%

Synthesis of Macrocyclic Compounds by Ring Closing Metathesis

Majumdar¹,

Rahaman²,

Roy

2007

COC

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Synthesis of macrocyclic compounds including natural products with varying complexities by ring closing metathesis is described. Twelve to very large rings that have been synthesized in moderate to good yields and the synthesis of larger rings as a part of bi-or poly-cyclic systems are also described in this review. The effectiveness of the Grubbs' catalyst towards the RCM in presence of free alcohols, epoxides as well as with various silyl ethers is also presented. In addition to these, the application of RCM towards the syntheses of various naturally occurring macrolides, lactams and unnatural cyclic poly ethers, catenanes etc. are described.

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A short route for the synthesis of “sweet” macrocycles via a click-dimerization–ring-closing metathesis approach

Abstract: A facile and flexible approach for the preparation of macrocyclic molecules containing different carbohydrate moieties is presented, employing the reaction cascade: click-dimerization and ring-closing metathesis.

Cited by 67 publications

References 26 publications

Alkynyl Ethers of Glucans: Substituent Distribution in Propargyl‐, Pentynyl‐ and Hexynyldextrans and ‐amyloses and Support for Silver Nanoparticle Formation

Alkynyl Ethers of Glucans: Substituent Distribution in Propargyl‐, Pentynyl‐ and Hexynyldextrans and ‐amyloses and Support for Silver Nanoparticle Formation

Polymer “Clicking” by CuAAC Reactions

Synthesis of Macrocyclic Compounds by Ring Closing Metathesis

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