Solid-Phase Organic Synthesis:  A Critical Understanding of the Resin

Vaino, Andrew R.; Janda, Kim D.

doi:10.1021/cc000046o

Cited by 163 publications

(122 citation statements)

References 164 publications

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“…Theoretically, the limited macromolecular relaxation by cross-linking site in the network reduces chain flexibility and elevates the T g of the beads [66] as well as decreasing the solvent swelling Table 6. Furthermore, the T g values of the synthesized copolymer beads for various toluene/heptane ratios of 100/0, 80/20, 60/40, 80/20 as diluents for the monomers are shown in Table 7.…”

Section: Resultsmentioning

confidence: 99%

A novel route for synthesis of cross-linked polystyrene copolymer beads with tunable porosity using guar and xanthan gums from bioresources as alternative synthetic suspension stabilizers

Rahmatpour

Goodarzi

Moazzez

2018

Designed Monomers and Polymers

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Cross-linked polymer beads with different cross-linking agent loading were prepared by carrying out cross-linking suspension copolymerization of styrene-divinylbenzene (St- DVB) monomers using guar gum (GG) and xanthan gum (XG) from bioresources as eco-friendly suspension biopolymer stabilizers in the presence of non reactive diluents. The effects of GG and XG as suspension biostabilizers on the characteristics of the styrene copolymer beads were investigated regarding thermal properties, porosity characteristics, solvent swelling ratio, and surface morphologies using TGA, DSC, XRD, SEM, BET analyses. Spherical and regular beads with smooth surface were produced and the average particle size was in the range 170–290 μm (50–80 mesh size). The porosity characteristics of the produced beads including surface area and pore volume were in range 0.45 m2/g and 32–45 ml/g, respectively. Overall, the present article provided a novel route to prepare cross-linked polystyrene copolymer beads with tunable porosity suitable for catalyst support.

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Section: Resultsmentioning

confidence: 99%

A novel route for synthesis of cross-linked polystyrene copolymer beads with tunable porosity using guar and xanthan gums from bioresources as alternative synthetic suspension stabilizers

Rahmatpour

Goodarzi

Moazzez

2018

Designed Monomers and Polymers

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“…Most notably adequate solvation of the solid-support, more commonly known as swelling, which is often considered as the most important prerequisite for SPOS [8]. Inadequate swelling will result in poor active site accessibility and diminished reaction rates, due to poor mass transfer between the bulk solution-phase and the solid-support [9].…”

Section: Introductionmentioning

confidence: 99%

Greener solvents for solid-phase organic synthesis

Lawrenson

2017

Pure and Applied Chemistry

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Solid-phase organic synthesis is an essential method for the rapid synthesis of complex biological structures and libraries of small organic molecules. However, it is often associated with the use of large quantities of problematic solvents for the removal of excess reagents and reaction by-products. Given that solvent will often be the biggest contributor to waste generated in the average pharmaceutical/fine-chemical process, its exchange for a more desirable alternative often presents the biggest gains in terms of reducing environmental impact. This review aims to explore recent approaches to performing solid-phase organic synthesis, and associated solid-phase peptide synthesis, in neoteric solvents and reaction media that present greener alternatives.

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“…1 The hydrolysis of acetate groups on SLURPS-Ac, 5 is already a point in case which reaches completion to give alcohol 6 in ethanol/water mixture under which PS gel supports collapse and perform poorly. [3][4][5][6][7][8][9][10][11][12][13] As relevant transformations, we identified the dihydroxylation of alkenes using catalytic amounts of OsO 4 in the presence of stoichiometric oxidants, 14 a key transformation in natural product synthesis and aldoximes formation, a vital intermediate step in synthetic sequences leading to important heterocyclic cores. [15][16][17][18][19] Results and discussion:…”

Section: Introductionmentioning

confidence: 99%

Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

et al. 2007

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Novel non-PEG derived polyether resins, coined SLURPS (Superior Liquid Uptake Resins forPolymer-supported Synthesis), were studied for their performance in solid-phase synthesis. Novel amino functional resins, SLURPS-NH 2 , were prepared with a loading of up to 8.5 mmol/g and employed successfully in the solid-phase synthesis of Leu-Enkephalin. The peptide was obtained with the same 2 purity when compared to its synthesis with commercial standard poly(dimethyl acrylamide) resins.Furthermore we show loading and cleavage of aromatic carboxylic acids in excellent yield. The advantageous solvent compatibility of our support was demonstrated through the biphasic dihydroxylation of alkenes with OsO 4 in t-BuOH/water mixtures producing bound 1,2-diols and synthesis and removal of a bound oxime using ethanol/water mixtures both in excellent yields. Reactions were easily monitored by gel-phase NMR and FTIR These results show that SLURPS are very well suited for organic transformations using highly polar solvent mixtures and reagents and this at much higher loading levels than standard amphiphilic resins of similar solvent compatibility. Graphical Abstract:O OH SLURPS

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Solid-Phase Organic Synthesis: A Critical Understanding of the Resin

Cited by 163 publications

References 164 publications

A novel route for synthesis of cross-linked polystyrene copolymer beads with tunable porosity using guar and xanthan gums from bioresources as alternative synthetic suspension stabilizers

A novel route for synthesis of cross-linked polystyrene copolymer beads with tunable porosity using guar and xanthan gums from bioresources as alternative synthetic suspension stabilizers

Greener solvents for solid-phase organic synthesis

Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

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