Literature DB >> 20337423

Long-range shielding effects in the (1)H NMR spectra of Mosher-like ester derivatives.

Thomas R Hoye1, Sara E Erickson, Sherrie L Erickson-Birkedahl, Christopher R H Hale, Enver Cagri Izgu, Michael J Mayer, Patrick K Notz, Matthew K Renner.   

Abstract

The relative magnitudes of the chemical shift differences (Deltadeltas) in the two diastereomers of menthyl esters of known chiral derivatizing agents (CDAs) were compared to those of the alpha-methoxy-alpha-trifluoromethyl-1-naphthylacetyl (MTN((1))A) analogues I. Discrimination of the terminal diastereotopic methyl resonances in esters of the homologous, symmetrical carbinols II was evaluated. Remarkably, the methyls differed in the MTN((1))A esters III even when n = 15; an unexpected crossover in the sign of the Deltadelta values was also observed.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20337423      PMCID： PMC2886499          DOI： 10.1021/ol1003862

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  3 in total

1.  (1-Naphthyl)(trifluoromethyl) O-carboxy anhydride as a chiral derivatizing agent: eclipsed conformation enforced by hydrogen bonding.

Authors:  Olivier Thillaye du Boullay; Aurélie Alba; Fatima Oukhatar; Blanca Martin-Vaca; Didier Bourissou
Journal:  Org Lett       Date:  2008-09-25       Impact factor: 6.005

2.  A "shortcut" Mosher ester method to assign configurations of stereocenters in nearly symmetric environments. Fluorous mixture synthesis and structure assignment of petrocortyne A.

Authors:  Dennis P Curran; Bin Sui
Journal:  J Am Chem Soc       Date:  2009-04-22       Impact factor: 15.419

3.  Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons.

Authors:  Thomas R Hoye; Christopher S Jeffrey; Feng Shao
Journal:  Nat Protoc       Date:  2007       Impact factor: 13.491
  3 in total
  2 in total

1.  Synthesis and spectroscopic analysis of a stereoisomer library of the phytophthora mating hormone α1 and derived bis-Mosher esters.

Authors:  Reena Bajpai; Dennis P Curran
Journal:  J Am Chem Soc       Date:  2011-11-28       Impact factor: 15.419

2.  Essential parameters for structural analysis and dereplication by (1)H NMR spectroscopy.

Authors:  Guido F Pauli; Shao-Nong Chen; David C Lankin; Jonathan Bisson; Ryan J Case; Lucas R Chadwick; Tanja Gödecke; Taichi Inui; Aleksej Krunic; Birgit U Jaki; James B McAlpine; Shunyan Mo; José G Napolitano; Jimmy Orjala; Juuso Lehtivarjo; Samuli-Petrus Korhonen; Matthias Niemitz
Journal:  J Nat Prod       Date:  2014-06-04       Impact factor: 4.050
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.