Argonaut Quest Training Workshop 2 (pdf) - Artisan Scientific

4Product: PS-DESChemical Name: Butyl diethylsilane polystyreneCapacity: 0.6 - 1.0 mmol/g (determined byreduction of trityl bromide and quantitation ofthe triphenyl methane produced)Bead Size: 100 - 200 mesh (75 - 150 microns)Resin Swelling: CH,Cl, (8.4 mL/g),THF (8.2mL/g), DMF (3.1 mL/g)Linker Functionality: Alcohols, carbonylgroups, acetylenes, aromatic compoundsReaction Conditions Tolerated: Acidic, basicTypical Cleavage Conditions:AcOH/THF/water (6:6: 1,50 - 80 deg. C) for primaryand secondary alcohols.TBAF (THF) orHF/pyridine/THF (25 deg. C) may also be used.Electron-rich and neutral aromatics cleaved usingTFMDCM, electron-poor using TBAE1Products: Alcohols, aromatics, acetylenes, heterocyclesRecommended Agitation: Gentle magnetic stirring,rocking, or overhead stirring for large resinquantities (> 5g)Part #Qty300142 10 g800143 25 g800 144 100 g8001 45 50 #3 ArgoCaps800 146 100 #3 ArgoCaps800147 500 #3 ArgoCaps800 148 1000 #3 ArgoCaps800184 50 #5 ArgoCaps800 185 100 #5 ArgoCaps800 186 500 #5 ArgoCaps800 187 1000 #5 ArgoCapsSilyl-derivatives are widely used to protect variousfunctional groups such as alcohols, phenols,carboxylic acids, amines, acetylenes, and aromaticcompounds." They are inert to a wide range ofsynthetic transformations, but can be easily removedunder selective conditions (e.g. HF/pyridine, fluorideion).Typically, they are produced by the reaction of asilyl chloride and the corresponding functionality(alcohol, carboxylic acid, acetylene, Grignard oralkyllithium derivatives).Polymer-supported silyl chlorides and arylsilanederivatives' have a number of limitations:Polymeric silyl chlorides are reactive and unstableto hydrolysis leading to poor shelf life.Displacement of silyl chlorides is difficult tomonitor using standard spectroscopic techniques.For many traceless applications, aromatic scaffoldsare attached to a silicon-containing handle whichis subsequently attached to the solid support.' "'Argonaut's PS-DES resin has a silane (Si-H) moietywhich offers a number of unique advantages:Stability to moisture for long shelf life.Direct attachment of functional groups (e.g.alcohol," carbonyl," aromatic, or unsaturatedderivatives) without prior transformation to -activated silylating agents (e.g. silyl chloride).Efficient transformation into a reactive silylchloride derivative which can be used immediately,before hydrolysis or degradation can occur.Ability to monitor reactions using IR spectroscopyby examination of the Si-H stretch (2100 cm-').PS-DES resin may be chlorinated to form the silylchloride derivative by treatment with trichloroiso-Figure 120 -PS DES Cl4000 3500 3000 2500 2000 1500Wavenumbers (cm-I)Artisan Technology Group - Quality Instrumentation ... Guaranteed | (888) 88-SOURCE | www.artisantg.com