Acyl Fluorides as Direct Precursors to Fluoride Ketyl Radicals: Reductive Deuteration using SmI2 and D2O

2021 ◽  
Author(s):  
Hengzhao Li ◽  
Mengqi Peng ◽  
Zemin Lai ◽  
Lei Ning ◽  
Xingyue Chen ◽  
...  
Keyword(s):  
Deuterium Incorporation

A highly chemoselective reductive deuteration of acyl fluorides to provide α,α-dideuterio alcohols with exquisite levels of deuterium incorporation was developped using SmI2 and D2O as deuterium source. This method introduces...

scholarly journals Isotopologue distributions of peptide product ions by tandem mass spectrometry: Quantitation of low levels of deuterium incorporation

2007 ◽  
Vol 367 (1) ◽  
pp. 40-48 ◽  
Author(s):  
Benlian Wang ◽  
Gang Sun ◽  
David R. Anderson ◽  
Minghong Jia ◽  
Stephen Previs ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Tandem Mass Spectrometry ◽  
Tandem Mass ◽  
Deuterium Incorporation ◽  
Product Ions ◽  
Low Levels ◽  
Peptide Product

scholarly journals Asymmetric and Regiospecific Synthesis of Isotopically Labelled Cyclopropane Fatty Acid (9R,10S)-Dihydrosterculic Acid: Overcoming Spontaneous Protonation During Lithium-Sulfoxide Exchange­

SynOpen ◽  
2018 ◽  
Vol 02 (02) ◽  
pp. 0168-0175
Author(s):  
Samuel Shields ◽  
Peter Buist ◽  
Jeffrey Manthorpe
Keyword(s):  
Fatty Acid ◽  
Total Synthesis ◽  
Cyclopropane Ring ◽  
Rapid Quenching ◽  
Cyclopropane Fatty Acid ◽  
Deuterium Incorporation ◽  
Biologically Relevant ◽  
Dihydrosterculic Acid

The total synthesis of isotopically labelled (9R,10S)-dihydro­sterculic acid, a usual cyclopropane fatty acid with biologically relevant toxicity upon desaturation in vivo, is reported. A diastereoselective Corey­–Chaykovsky reaction was employed to form the cyclopropane ring. Rapid quenching of a lithium-sulfoxide exchange was required to achieve the requisite high levels of deuterium incorporation.

ChemInform Abstract: DEUTERIUM INCORPORATION VIA ZINC-COPPER COUPLE REDUCTIONS OF HALIDES

1974 ◽  
Vol 5 (46) ◽  
pp. no-no
Author(s):  
R. M. BLANKENSHIP ◽  
K. A. BURDETT ◽  
J. S. SWENTON
Keyword(s):  
Deuterium Incorporation

Steric Course of Deuterium Incorporation from [2-2H2]Manlonyl-CoA into Fatty Acids by Fatty Acid Synthetases1

1981 ◽  
Vol 90 (6) ◽  
pp. 1697-1704 ◽  
Author(s):  
Kazuki SAITO ◽  
Akihiko KAWAGUCHI ◽  
Yousuke SEYAMA ◽  
Tamio YAMAKAWA ◽  
Shigenobu OKUDA
Keyword(s):  
Fatty Acids ◽  
Fatty Acid ◽  
Deuterium Incorporation

A New Method of Deuterium Incorporation to TMS-Epoxyalcohol Using Sodium Methylsulfinylmethylide-d5 (NaDMSO-d5)

Heterocycles ◽  
2018 ◽  
Vol 97 (1) ◽  
pp. 574
Author(s):  
Yuichi Kobayashi ◽  
Yutaro Nanba ◽  
Shuhei Tanabe
Keyword(s):  
New Method ◽  
Deuterium Incorporation

ChemInform Abstract: REGIOSPECIFIC DEUTERIUM INCORPORATION VIA THE REDUCTION OF TOSYLHYDRAZONES TO THE CORRESPONDING METHYLENE DERIVATIVES

1977 ◽  
Vol 8 (21) ◽  
pp. no-no
Author(s):  
G. W. KABALKA ◽  
D. T. C. YANG ◽  
J. H. CHANDLER ◽  
J. D. JUN. BAKER
Keyword(s):  
Deuterium Incorporation

Preparation of 1'-C Deuterated Synthons for RNA Synthesis by H-Phosphonate Method Aiming at Two-Dimensional NMR Secondary Structure Studies

1996 ◽  
Vol 61 (3) ◽  
pp. 389-403 ◽  
Author(s):  
Luboš Arnold ◽  
Martina Pressová ◽  
David Šaman ◽  
Martin Vogtherr ◽  
Stefan Limmer
Keyword(s):  
Secondary Structure ◽  
Rna Synthesis ◽  
2D Nmr ◽  
Two Dimensional ◽  
Deuterium Incorporation ◽  
Spectral Pattern ◽  
Step Procedure ◽  
Noesy Spectra

1'-C Deuterated H-phosphonate synthons were prepared via a 12-step procedure starting from [1'-2H]ribose. The procedure included nucleosidation of 1'-O-acetyl-2',3',5'-O-tribenzoyl[1'-2H]ribose with appropriately protected nucleobases and preparation of nucleoside-H-phosphonates by slightly modified described procedures. The automated RNA synthesis of 5'-G*C*U*A*U*UUAU-3' and 3'-AC*G*A*U*A*AAGU-5' was performed on a Gene Assembler Plus DNA-synthesizer. These specifically deuterated oligoribonucleotides were subsequently compared with the corresponding non-deuterated sequences using 2D-NMR NOESY spectra. Specific deuterium incorporation resulted in the expected simplification of spectral pattern.

Nuclear magnetic resonance studies. XL. Tricyclooctanone rearrangement, [3.2.1.0] → [3.3.0.0], via γ-enolization and a 2Hmr study of H/D exchange in tricyclic ketones

1984 ◽  
Vol 62 (7) ◽  
pp. 1385-1391 ◽  
Author(s):  
A. K. Cheng ◽  
Ashim K. Ghosh ◽  
J. B. Stothers
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Membered Ring ◽  
Deuterium Incorporation ◽  
Magnetic Resonance Studies ◽  
Endo Isomer ◽  
Exchange Processes ◽  
Initial Transformation ◽  
Nuclear Magnetic

The effect of strongly basic conditions (t-BuO−/t-BuOH/185 °C) on the exo and endo isomers of 7,7-dimethyltri-cyclo[3.2.1.02.4]octan-6-one has been examined. While the exo isomer is stable, the endo isomer readily rearranges to 4,4-dimethyltricyclo[3.3.0.02.8]octan-3-one (6) which subsequently undergoes reduction of the three-membered ring. The initial transformation is one of very few examples of γ-enolate rearrangement. Experiments in tert-buiyl alcohol-O-d1 were carried out to establish the several sites of deuterium incorporation in the initial ketones and in 6 using 2Hmr. These results reveal the stereochemistry of γ-enolate formation and cleavage as well as the stereoselectivities and relative rates of the exchange processes.

DBU-Catalyzed Deconjugation of 7-Substituted 3,4-Didehydro-2-oxepanones. Deuterium Incorporation, Significance of the Imine Double Bond, and Application to the Synthesis of a Key Pharmacophore

1998 ◽  
Vol 63 (2) ◽  
pp. 287-294 ◽  
Author(s):  
Duraiswamy A. Jeyaraj ◽  
Kamal K. Kapoor ◽  
Veejendra K. Yadav ◽  
Harsh M. Gauniyal ◽  
Masood Parvez
Keyword(s):  
Double Bond ◽  
Deuterium Incorporation
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