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Bare-minimum fluorous mixture synthesis of a stereoisomer library of 4,8,12-trimethylnonadecanols and predictions of NMR spectra of saturated oligoisoprenoid stereoisomers

Yeh, EAH and Kumli, E and Damodaran, K and Curran, DP (2013) Bare-minimum fluorous mixture synthesis of a stereoisomer library of 4,8,12-trimethylnonadecanols and predictions of NMR spectra of saturated oligoisoprenoid stereoisomers. Journal of the American Chemical Society, 135 (4). 1577 - 1584. ISSN 0002-7863

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Abstract

All four diastereomers of a typical saturated oligoisoprenoid, 4,8,12-trimethylnonadecanol, are made by an iterative three-step cycle with the aid of traceless thionocarbonate fluorous tags to encode configurations. The tags have a minimum number of total fluorine atoms, starting at zero and increasing in increments of one. With suitable acquisition and data processing, each diastereomer exhibits characteristic chemical shifts of methyl resonances in its 1H and 13C NMR spectra. Together, these shifts provide a basis to predict the appearance of the methyl region of the spectrum of every stereoisomer of higher saturated oligoisoprenoids. © 2013 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Yeh, EAH
Kumli, E
Damodaran, K
Curran, DPcurran@pitt.eduCURRAN
Date: 30 January 2013
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 135
Number: 4
Page Range: 1577 - 1584
DOI or Unique Handle: 10.1021/ja311606u
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
MeSH Headings: Fatty Alcohols--chemical synthesis; Fatty Alcohols--chemistry; Fluorine--chemistry; Magnetic Resonance Spectroscopy; Models, Molecular; Molecular Structure; Small Molecule Libraries--chemical synthesis; Small Molecule Libraries--chemistry; Stereoisomerism
Other ID: NLM NIHMS436128, NLM PMC3560418
PubMed Central ID: PMC3560418
PubMed ID: 23297872
Date Deposited: 18 Jul 2014 21:17
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/22251

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