?url_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rft.relation=http%3A%2F%2Fd-scholarship-dev.library.pitt.edu%2F10646%2F&rft.title=Fluorous+Mixture+Synthesis+(FMS)+of+Four+Isomers+of+4%2C8%2C12%2C-Trimethylnonadecanol+and+the+Development+of+an+NMR-based+Method+for+Determining+the+Configurations+of+Polyisoprenoid+Structures&rft.creator=Yeh%2C+An-Hung+E.&rft.description=The+chiral+polyisoprenoid+motif+has+been+identified+in+various+natural+products+such+as+vitamin+E%2C+chlorophyll-d%2C+and+beta-mannosyl+phosphomycoketide.+This+motif+features+stereocenters+bearing+branched+methyl+groups+at+every+fourth+carbon+of+a+long+alkyl+chain.+Due+to+the+lack+of+function+group%2C+assigning+the+configurations+of+these+structures+is+difficult.%0D%0AHerein%2C+we+describe+the+fluorous+mixture+synthesis+(FMS)+of+the+4S%2C8S%2C12S-%2C+4S%2C8R%2C12S-%2C+4R%2C8S%2C12S-%2C+and+4R%2C8R%2C12S-trimethylnonadecanol+isomers.+The+FMS+features+a+new+family+of+ultra-light+fluorous+O-phenyl+thionocarbonate+tags+and+employees+the+most+efficient+fluorous+tagging+strategy+to+date.+The+analyses+of+these+four+isomers+were+found+to+exhibit+small+but+reliable+differences+in+1H+and+13C+NMR+spectra.+Furthermore%2C+these+chemical+shifts+of+the+branched+methyl+groups+were+diagnostic+of+relative+configurations.+By+deducing+the+relative+relationship+between+configuration+and+chemical+shift%2C+we+developed+predictions+of+4%2C8%2C12%2C16-tetramethyltricoanol%2C+and+4%2C8%2C12%2C16%2C20-pentamethyl-heptacosanol.&rft.date=2012-02-01&rft.type=University+of+Pittsburgh+ETD&rft.type=PeerReviewed&rft.format=application%2Fpdf&rft.language=en&rft.identifier=http%3A%2F%2Fd-scholarship-dev.library.pitt.edu%2F10646%2F2%2FYehFinalDissertation-1.pdf&rft.identifier=++Yeh%2C+An-Hung+E.++(2012)+Fluorous+Mixture+Synthesis+(FMS)+of+Four+Isomers+of+4%2C8%2C12%2C-Trimethylnonadecanol+and+the+Development+of+an+NMR-based+Method+for+Determining+the+Configurations+of+Polyisoprenoid+Structures.++Doctoral+Dissertation%2C+University+of+Pittsburgh.++++(Unpublished)++