Synthesis of new cores and their use in the preparation of polyester dendrimers

Twibanire, Jean-d’Amour K.; Al-Mughaid, Hussein; Grindley, T. Bruce

doi:10.1016/j.tet.2010.10.018

Cited by 16 publications

(29 citation statements)

References 59 publications

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“…Restricting the mobility of the alcohol-terminated chains through formation of a cyclic acetal decreases steric hindrance during ester formation, allowing facile access to high generation dendrimers [129]. Using NMR parameters, we have recently established that the configuration of the O-benzylidene derivative of 2,2'-bis(hydroxymethyl)propanoic acid is cis [130]. Scheme 9.…”

Section: Methods Used For Ester Bond Formationmentioning

confidence: 99%

“…Polyester dendrimers were prepared up to the fourth generation using even sterically congested cores like pentaerythritol in good yields using DMAP and DCC to promote ester formation. Since then, a number of research groups have utilized the benzylidene-protected bis-HMPA as a convenient building block [127,129,130,146,[150][151][152][153]. Synthesis of a dendritic macro-initiator for atom transfer radical polymerization [146].…”

Section: Scheme 12mentioning

confidence: 99%

“…We have synthesized tribranched dendrons in order to prepare dendrimers that have denser layers than those derived from bis-HMPA (Scheme 52) [130,219]. Polyester dendrimers with denser layers are likely to be longer lived under physiological conditions.…”

Section: The Use Of Other Aliphatic Dendronsmentioning

confidence: 99%

“…As shown in Scheme 53, we have recently used the TsEt protecting group in the synthesis of a second generation acid dendron [134]. A tri-branched acid anhydride dendron 115 [130] was reacted with TsEtOH in the presence of DMAP to give benzyl-protected first generation 117. Hydrogenolysis then gave 118 in good yield.…”

Section: The Use Of Other Aliphatic Dendronsmentioning

confidence: 99%

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Polyester Dendrimers

Twibanire

Grindley

2012

Polymers

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Polyester dendrimers have been comprehensively reviewed starting from their first synthesis in the early 1990s by Hawker and Fréchet. Polyester dendrimers have attracted and continue to attract extensive interest because they are comparatively easy to make and because, whenever they have been tested, they have been found to be non-toxic. A number of different strategies for their synthesis have been examined and the methods employed for formation of the ester bond during dendrimer assembly have been summarized. The newest approaches, including the use of bifunctional orthogonally reacting dendrons and accelerated synthesis have been surveyed.

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Section: Methods Used For Ester Bond Formationmentioning

confidence: 99%

Section: Scheme 12mentioning

confidence: 99%

Section: The Use Of Other Aliphatic Dendronsmentioning

confidence: 99%

Section: The Use Of Other Aliphatic Dendronsmentioning

confidence: 99%

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Polyester Dendrimers

Twibanire

Grindley

2012

Polymers

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“…In addition, polyester dendrimers have labile ester functionalities which are steadily hydrolyzed in vivo to release entrapped or covalently attached drugs. Higher generation polyester dendrimers can easily be prepared with facile synthesis of other dendrimers and a variety of methods have been reported for ester bond formation [126][127][128][129][130][131][132][133][134][135]. The synthesis of polyester dendrimers in general [135] and those derived from bis-2,2-hydroxymethylpropanoic acid (bis-HMPA) in particular [58] have been reviewed.…”

Section: Attractive Features Of Polyester Dendrimers For Drug Delivermentioning

confidence: 99%

Polyester Dendrimers: Smart Carriers for Drug Delivery

Twibanire

Grindley

2014

Polymers

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Polyester dendrimers have been shown to be outstanding candidates for biomedical applications. Compared to traditional polymeric drug vehicles, these biodegradable dendrimers show excellent advantages especially as drug delivery systems because they are non-toxic. Here, advances on polyester dendrimers as smart carriers for drug delivery applications have been surveyed. Both covalent and non-covalent incorporation of drugs are discussed.

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Carbonylation as a Key Step in New Tandem Reactions – A Route to BODIPYs

Miller,

Impelmann,

Bauer

et al. 2024

Chemistry A European J

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Herein, a highly efficient five‐step reaction sequence to BODIPYs is presented. The key step is the combination of transition metal‐catalyzed in‐situ generation of aldehydes and their subsequent organocatalytic activation to yield dipyrromethanes, which are further converted to the corresponding BODIPY. Classic syntheses towards BODIPYs have relied on aldehydes or acid chlorides, which are often not commercially available and rather sensitive to handle. The presented approach starts from readily available and stable alkenes or aryl‐bromides, which allows to extend the range of readily available BODIPYs that can be tailored for their specific use. The synthesis of 55 derivatives with overall yields of up to 78% demonstrates the wide applicability and advantages of the presented method.

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Synthesis of new cores and their use in the preparation of polyester dendrimers

Cited by 16 publications

References 59 publications

Polyester Dendrimers

Polyester Dendrimers

Polyester Dendrimers: Smart Carriers for Drug Delivery

Carbonylation as a Key Step in New Tandem Reactions – A Route to BODIPYs

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