Full and partial differentiation of tris-1,1,1-(hydroxymethyl)ethane via direct and indirect methodology

Clarke, P.; Jeffery, Martin J.; Boydell, A. James; Whiting, Sally; Linclau, Bruno

doi:10.1016/j.tet.2004.02.056

Cited by 10 publications

(7 citation statements)

References 46 publications

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“…The synthesis of 7 began by coupling mono-TBDMSprotected 1,1,1-tris(hydroxymethyl)ethane 16 and [G-3] acid chloride dendron 3 17 to produce dendrimer 4 (Scheme 1). Deprotection of the silyl group followed by cross-linking with first generation Grubbs catalyst 1 at high dilution produced didendron 6, which was fully cross-linked.…”

Section: Resultsmentioning

confidence: 99%

Exploring the Reversibility of the Ring-Closing Metathesis Mediated Cross-linking of Dendrimers

2007

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Section: Resultsmentioning

confidence: 99%

Exploring the Reversibility of the Ring-Closing Metathesis Mediated Cross-linking of Dendrimers

2007

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“…The malonaldehydes 1 – 3 (see Table 1) used in this study were synthesized in quantitative yield6a,b by IBX‐mediated (IBX= o ‐iodoxybenzoic acid) oxidation6c,d of the corresponding 1,3‐diols, which were easily obtained from exceedingly cheap tris‐1,1,1‐(hydroxymethyl)ethane 6a,b…”

Section: Chelation‐controlled Allylstannation Reactions Of Malonaldehmentioning

confidence: 99%

Stereoarrays with an All‐Carbon Quaternary Center: Diastereoselective Desymmetrization of Prochiral Malonaldehydes

Linclau¹,

Cini²,

Oakes³

et al. 2011

Angewandte Chemie

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Durch Chelatisierung von MgBr2 „gezähmte“ prochirale Malonaldehyde gehen diastereoselektive Monoadditionen mit Allylstannanen ein (siehe Schema; PG=Schutzgruppe, TBDMS=tert‐Butyldiphenylmethylsilyl, Tr=Trityl). Durch die anschließende Addition eines zweiten Nucleophils in demselben Reaktionsgefäß gelangt man hoch diastereoselektiv zu unsymmetrischen Produkten mit bis zu fünf benachbarten Stereozentren (eines davon ein quartäres Kohlenstoffzentrum).

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“…To carry out selective functionalizations on each of the three hydroxyl groups, a ketal protecting group was selected to mask two of the alcohols. 3 Ketal protecting groups have seen extensive use for the protection of 1,2-and 1,3-diols for a wide range of applications including the selective modification of carbohydrates, 4 the synthesis of natural products, 5 the production of deep UV photoresists, 6 and the preparation of hydroxylated dendrimers. 7 The benzylidene ketal was chosen specifically because of its unique ability to be partially cleaved, exposing one of the alcohols, and leaving the other one protected as a benzyl ether.…”

mentioning

confidence: 99%

“…3 Well resolved differences in their 1 H NMR spectra, particularly of the acetal hydrogen (5.42 ppm for cis vs 5.39 ppm for trans) and the methyl hydrogens (0.80 ppm for cis vs 1.31 ppm for trans), enabled the product ratios to be easily determined using 1 H NMR. NMR integration studies confirm that the polarity of the reaction solvent significantly affects the ratio of isomers.…”

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Synthesis of a pH-independent bifurcated amphiphile

Willham

Laurent

Grayson

2008

Tetrahedron Letters

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An efficient synthetic method for preparing bifurcated amphiphiles has been developed such that the functionality for attachment is located at the interface between the lipophilic and hydrophilic side chains. Attachment of the amphiphile to the repeat units of polymeric substrates enables the rapid preparation of amphiphilic homopolymers. Keywordsamphiphile; amphiphilic monomer; amphiphilic polymer; amphiphilic homopolymerThe human production and use of amphiphilic compounds dates to prehistory, when triacylglycerides were hydrolyzed in alkaline solution affording soaps to enable the aqueous dispersion of lipids. Since that time amphiphiles have seen widespread use owing to their unique ability to modulate the surface properties of molecules, particles, or solid surfaces with respect to their environment. Amphiphilic materials also can be used to enhance medical technologies, from their encapsulation of potent but insoluble drugs in micellar carriers, to their disruption of fungal cell walls. Much effort has focused on the synthesis and applications of amphiphilic block copolymers; however, an equally promising but relatively under-explored architectures include amphiphilic homopolymers 1 and dendrimers, 2 in which each repeat unit bears both lipophilic and hydrophilic sidechains. If amphiphilic homopolymers can organize into discrete nanoscale reverse micelles, they offer promise as carriers to transport polar therapeutics through the lipophilic stratum corneum, thereby enhancing transdermal drug delivery.The traditional oral route for delivering drugs is incompatible with many therapeutics due to the harshly acidic and enzymatically active gastric environment, therefore efforts have shifted to investigate technologies that would allow the transdermal administration of these materials. While the lipids within the skin are permeable to small, lipophilic molecules, most therapeutics are required to be hydrophilic to permit their distribution throughout the body via the bloodstream. However, only a handful of therapeutics exhibits the amphiphilic character that affords both permeability through the skin and systemic delivery through the bloodstream. Amphiphilic carriers can be designed to compatibilize polar drugs with the skin lipids to enable their transdermal transport, while allowing their release once they reach the bloodstream.In order to probe the efficacy of amphiphilic homopolymers for improving transdermal drug delivery, a broad range of polymer sizes and architectures should be explored. The first step towards this goal is the development of an efficient synthetic method for preparing bifurcated * Corresponding author. Tel.: +1-504-862-8135; fax: +1-504-865-5596; e-mail: sgrayson@tulane.edu. Publisher's Disclaimer: This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in i...

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Full and partial differentiation of tris-1,1,1-(hydroxymethyl)ethane via direct and indirect methodology

Cited by 10 publications

References 46 publications

Exploring the Reversibility of the Ring-Closing Metathesis Mediated Cross-linking of Dendrimers

Exploring the Reversibility of the Ring-Closing Metathesis Mediated Cross-linking of Dendrimers

Stereoarrays with an All‐Carbon Quaternary Center: Diastereoselective Desymmetrization of Prochiral Malonaldehydes

Synthesis of a pH-independent bifurcated amphiphile

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