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
![[img]](http://d-scholarship.pitt.edu/style/images/fileicons/text_plain.png) |
Plain Text (licence)
Available under License : See the attached license file.
Download (1kB)
|
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.
Share
Citation/Export: |
|
Social Networking: |
|
Details
Item Type: |
Article
|
Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID  |
---|
Yeh, EAH | | | | Kumli, E | | | | Damodaran, K | | | | Curran, DP | curran@pitt.edu | CURRAN | |
|
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: |
22 Jun 2021 12:56 |
URI: |
http://d-scholarship.pitt.edu/id/eprint/22251 |
Metrics
Monthly Views for the past 3 years
Plum Analytics
Altmetric.com
Actions (login required)
 |
View Item |