Phase-transfer synthesis of monoalkyl ethers of oligoethylene glycols

Gibson, Thomas

doi:10.1021/jo01294a034

Cited by 68 publications

(42 citation statements)

References 3 publications

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“…It started with the monobenzylation of 1,5-pentanediol (15) (18). The resulting mono alcohol 16 was subjected to the modified Williamson ether synthesis (19), which involved the vigorous mixing of a two-phase system containing 16, 1-bromo-2-tetrahydropyranyloxylethane, and aqueous sodium hydroxide in the 14, R = H 8, R = TBDMS presence of a phase transfer catalyst, tetrabutylammonium hydrogen sulfate.…”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of analogues of ionomycin

Hu¹,

Weller²

1994

Can. J. Chem.

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THOMAS Q. HU and LARRY WEUER. Can. J. Chem. 72, 1500Chem. 72, (1994.Based on the analysis of the crystal structure of the ~a ' + salt of ionomycin and the chemical and physical data on ionomycin, a number of ionomycin analogues have been synthesized to study the structural features affecting the Ca'+ binding and transport. Compounds 2,3, and 4 were synthesized to study the effect of additional intramolecular oxygen coordination sites on ~a ' + transport. Compounds 5a-Sd were prepared to study the effect of lipid solubility on ~a ' + binding aild transport. Compounds 6ri-6c were prepared to study the effect of the distance between the P-diketone and the carboxyl group on ~a ' + transport. A general synthetic route to these compounds has been developed. The key reactions in this route are the consecutive legioselective alkylations of the dianion of 2,4-pentanedione with the appropriate bromides.

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Section: Resultsmentioning

confidence: 99%

Design and synthesis of analogues of ionomycin

Hu¹,

Weller²

1994

Can. J. Chem.

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“…The reaction of an 11-bromoundec-1-ene with a slight excess of 50% sodium hydroxide and 10 equiv of tetra(ethy1ene glycol) provided the monoether 1 [23] and tert-butyl bromoacetate was introduced to provide the protected carboxylate group [24]. Radical addition of thioacetic acid to the double bond gave the thioacetate 3 in good yield [25].…”

Section: Methodsmentioning

confidence: 99%

Guided Assemblies of Ferritin Nanocages: Highly Ordered Arrays of Monodisperse Nanoscopic Elements

Hu¹,

Chen²,

Park³

et al. 2010

Advanced Materials

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Patterning and immobilizing protein biomolecules with nanosized dimension is important in the development of applications ranging from biochip arrays [1][2][3] and biosensors [4][5][6] to electronic devices. [7,8] Protein nanocages, such as horse spleen ferritin, HSF, (12 nm in diameter) with magnetic cores (8 nm in diameter), [9] have the distinct advantage over synthetic nanoparticles of being truly monodisperse in size and shape. In addition, by controlling pH, the charge on the nanocages can be manipulated, providing additional control over the interparticle separation. Provided planar, ordered arrays of the nanocages can be achieved, these attributes can be used to generate two-dimensional arrays of nanoscopic elements, in which each element is exactly the same size and shape, and the areal density and lateral packing can be manipulated by the charge on the nanocage surface. Such a strategy provides an unique pathway to overcome some of the current technological limitations in generating addressable media.[10] In the case of HSF, the iron core can be removed and replaced with other metals, like magnetite, manganese oxide, uranyl oxide, and cadmium sulfide quantum dots, [11] which further broadens their potential applications.Two-dimensional arrays of HSF have been produced at an air/ liquid interface. [12][13][14] However, practical application requires the transfer of the HSF arrays to a solid substrate, which introduces defects and disorder. Recently, an evaporation-induced convective assembly method [15] was developed to produce robust HSF arrays directly on the solid substrate by a spread-coating technique. However, achieving long-range lateral order, and controlling the orientation of the lattice formed by the assembly is difficult, making the transition to applications impractical.Here, we address these issues with planar silicon oxide substrates, prepatterned with gold nanodots that preferentially interact with end-functional thiol groups on a tether attached to the HSF. The separation distance between the nanodots was sufficient to preclude one HSF from bridging two adjacent gold nanodots, and the length of the tether was designed so that only one HSF could anchor to each gold nanodot.There are numerous routes by which arrays of gold nanodots can be prepared on planar silicon wafers, ranging from e-beam lithographic to electro-oxidative atomic force microscopic methods. However, to generate ordered arrays over large surface areas without loss of structural fidelity due to writing errors, highly parallel, self-assembly processes are required. Block copolymer (BCP) micelle lithography [16] provides a rapid, high-throughput method to fabricate arrays of regularly spaced nanodots with high areal density and lateral ordering. Here, polystyrene-block-poly(4-vinylpyridine) (PS-b-P4VP) diblock copolymer micelles [17] were spin-coated on silicon wafers or glass substrates to form uniform, monolayered micellar films that, upon annealing in a saturated tetrahydrofuran (THF) vapor environment, produced an array ...

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“…1 1 Synthesis of 2-f2-(2-Allyloxyethoxyethoxyjethanol 2-[2-(2-Allyloxycthoxy)ethoxy]ethanol was synthesized according to a modified literature procedure. 12 Its detailed synthesis and characterization will ue described elsewhere. 13 …”

Section: Methodsmentioning

confidence: 99%