Argonaut Quest Training Workshop 2 (pdf) - Artisan Scientific

Scientific Resources Page 8 of 10Kaldor, S.W.; Siegel, M.G.,Current Opinion in Chemical Biology, 1997,1:IOl-106."Non-Acidic Cleavage of Wang-Derived Ethers From SolidSupport: Utilization of a Mixed-Bed Scavenger for DDQ"Deegan, T.; Gooding, 0.; Baudart, S.; Porco, J.A. , Jr., TetrahedronLetters, Vol. 38, No. 28, pp. 4973-4976, 1997.Ethers derived from ArgoGel Wang Chloride resin have been prepared and evaluated in bothtrifluoroacetic acid and DDQ-mediated cleavage protocols. DDQ cleavage of resin bound p-alkoxy benzyl ethers has been found to circumvent problems associated withtrifluoroacetylation of alcohol products during TFA treatment. In order to facilitate the removalof excess DDQ and DDQH from cleaved products, a mixed bed ion exchange scavenger hasbeen developed.Related Argonaut Product: ArqoGeI Wang-Cl"Tandem UPS: Sequential Mono- and Dialkylation of Resin-BoundGlycine via Automated Synthesis"Gnffith, D.; O'Donnell, M.; Pottorf, R.; Scott, W.; Porco, J.A.,Jr.,Tetrahedron Letters, Vol. 38, No 51, pp. 8821-882, 1997.A method has been developed for the synthes~s of racemlc a.a-dwbst~tuted ammo ac~ds bya tandem alkylat~on process ("Tandem UPS") on sohd support Consecut~ve alkylat~ons ofWang resm-bound benzophenone mnes of glycme afforded unnatural, dwbst~tuted ammoac~der~vat~ves Automated chem~cal synthes~s was used to effic~ently opt~m~ze cond~t~onsfor both format~on and hydrolys~s of resm bound d~subst~tuted benzophenone lmlnes and togenerate a matr~x of d~subst~tuted ammo ac~der~vat~ves"The Solid Phase Synthesis of Trisubstituted 1,4-Diazabicyclo(4.3.0)nonan-2-one Scaffolds: On Bead Monitoring of HeterocycleForming Reactions Using '=N NMR"Swayze, E., Tetrahedron Letters, Vol. 38, No 50, pp. 8643-8646, 1997.Several representative 3.4,8-trisubstituted 1,4-diazabicyclo(3,4,O)nonan-2-ones have beenprepared employing solid phase smethodologies. Elaboration of a 4-hydroxyproline derivativewith an '5~-amino acid derivative allowed convenient monitoring of the reaction sequence onsolid support by gel-phase I5N NMR. An intramolecular Mitsunobu cyclization provided thedesired heterocycle, which could be further functionalized at the 4-position. This syntheticmethod is facile, general and suitable for the construction of large libraries of compounds forbiological assaysRelated Argonaut Product: ArgoGel-OH"Secondary Amide-based Linkers for Solid Phase OrganicSynthesis"Swayze, E., Tetrahedron Letters, Vol. 38, No. 49, pp. 8465-8468,1997.The electron rich benzaldehyde derivatives 4-hydroxybenzaldehyde and 2-methoxy-4-hydroxybenzaldehyde have been investigated for use as linkers for solid phase organicsynthesis. Reductive amination of these aldehydes attached to ArgoGel resins with a modelprimary amine ggave the corresponding benzylic secondary amines. These compounds werethen converted to the corresponding ureas, sulfonamides, aryl amides, and alkyl amides byderivatization with an appropriate electrophile. The desired secondary amide derivative wasthen cleaved from the support by treatment with trifluoroacetic acid to provide essentiallyquantitative yields of products in high purityRelated Argonaut Product: ArgoGel MB-CHOArtisan Technology Group - Quality Instrumentation ... Guaranteed | (888) 88-SOURCE | www.artisantg.com