172995-33-4Relevant academic research and scientific papers
Anodic oxidation of dithiane carboxylic acids: A rapid and mild way to access functionalized orthoesters
Denis, Camille,Dobbs, Adrian P.,Garcia, Anthony D.,Goodall, Iain C. A.,Lam, Kevin,Leech, Matthew C.,Petti, Alessia
supporting information, p. 4000 - 4005 (2020/06/08)
A new electrochemical methodology has been developed for the preparation of a wide variety of functionalized orthoesters under mild and green conditions from easily accessible dithiane derivatives. The new methodology also offers an unprecedented way to access tri(fluorinated) orthoesters, a class of compound that has never been studied before. This provides the community with a rapid and general method to prepare libraries of functionalized orthoesters from simple and readily available starting materials.
Fenton-Inspired C-H Functionalization: Peroxide-Directed C-H Thioetherification
Groendyke, Brian J.,Modak, Atanu,Cook, Silas P.
, p. 13073 - 13091 (2019/10/10)
Substoichiometric iron mediates the thioetherification of unactivated aliphatic C-H bonds directed by resident silylperoxides. Upon exposure to a catalytic amount of iron(II) triflate, TIPS-protected peroxides bearing primary, secondary, and tertiary C-H sites undergo chemoselective thioetherification of remote C-H bonds with diaryl disulfides. The reaction demonstrates a broad substrate scope and functional group tolerance without the use of any noble metal additives. Mechanistic experiments suggest that the reaction proceeds through 1,5-H atom abstraction by a hydroxyl radical generated with iron.
(R)-N-(1-Methyl-2-hydroxyethyl)-13-(S)-methyl-arachidonamide (AMG315): A Novel Chiral Potent Endocannabinoid Ligand with Stability to Metabolizing Enzymes
Liu, Yingpeng,Ji, Lipin,Eno, Marsha,Kudalkar, Shalley,Li, Ai-Ling,Schimpgen, Marion,Benchama, Othman,Morales, Paula,Xu, Shu,Hurst, Dow,Wu, Simiao,Mohammad, Khadijah A.,Wood, Jodianne T.,Zvonok, Nikolai,Papahatjis, Demetris P.,Zhou, Han,Honrao, Chandrashekhar,MacKie, Ken,Reggio, Patricia,Hohmann, Andrea G.,Marnett, Lawrence J.,Makriyannis, Alexandros,Nikas, Spyros P.
supporting information, p. 8639 - 8657 (2018/10/02)
The synthesis of potent metabolically stable endocannabinoids is challenging. Here we report a chiral arachidonoyl ethanolamide (AEA) analogue, namely, (13S,1′R)-dimethylanandamide (AMG315, 3a), a high affinity ligand for the CB1 receptor (Ki o
Visible-light-mediated conversion of alcohols to halides
Dai, Chunhui,Narayanam, Jagan M.R.,Stephenson, Corey R.J.
experimental part, p. 140 - 145 (2012/02/06)
The development of new means of activating molecules and bonds for chemical reactions is a fundamental objective for chemists. In this regard, visible-light photoredox catalysis has emerged as a powerful technique for chemoselective activation of chemical bonds under mild reaction conditions. Here, we report a visible-light-mediated photocatalytic alcohol activation, which we use to convert alcohols to the corresponding bromides and iodides in good yields, with exceptional functional group tolerance. In this fundamentally useful reaction, the design and operation of the process is simple, the reaction is highly efficient, and the formation of stoichiometric waste products is minimized.
Primary alkyl bromides from dimethylthiocarbamates
Moynihan, Meghan F.,Tucker, Joseph W.,Abelt, Christopher J.
experimental part, p. 3565 - 3568 (2009/06/18)
The conversion of primary alkyl dimethylthiocarbamates into alkyl bromides using the Vilsmeier reagent occurs in high yields in the presence of other non-acid sensitive and non-nucleophilic functional groups. Georg Thieme Verlag Stuttgart · New York.
Synthesis and biological properties of tensyuic acids B, C, and E, and investigation of the optical purity of natural tensyuic acid B
Matsumaru, Takanori,Sunazuka, Toshiaki,Hirose, Tomoyasu,Ishiyama, Aki,Namatame, Miyuki,Fukuda, Takashi,Tomoda, Hiroshi,Otoguro, Kazuhiko,Omura, Satoshi
, p. 7369 - 7377 (2008/12/20)
The first, concise total synthesis of (±)-tensyuic acids B, C, and E, using chemoselective formal SN2′ type Grignard reactions and selective esterification, is described. In addition, the optical purity of natural (±)-tensyuic acid B was determined using Chirabite-AR. Synthetic tensyuic acids, together with their intermediate compounds, were found to possess useful bioactive properties, with some of them showing potent activity against Trypanosoma brucei brucei strain GUTat 3.1.
Synthesis of a polymer-bound galactosylamine and its application as an immobilized chiral auxiliary in stereoselective syntheses of piperidine and amino acid derivatives
Zech, Gernot,Kunz, Horst
, p. 4136 - 4149 (2007/10/03)
A 2,3,4-tri-O-pivaloylated β-D-galactopyranosyl azide bearing a hydroxy-functionalized spacer unit at the C-6 position of the galactose was synthesized and immobilized on the solid phase by using a polymer-bound chlorosilane. The azide was reduced to the
Stereoselective solid-phase synthesis of chiral piperidine derivatives by using an immobilized galactose auxiliary
Zech, Gernot,Kunz, Horst
, p. 787 - 790 (2007/10/03)
The fluoride-labile anchoring of a galactosylamine enabled the first stereoselective solid-phase combinatorial synthesis of didehydropiperidinones 1. The piperidine derivatives formed by asymmetric domino Mannich-Michael condensation at ambient temperatur
A mild, phosphine-free method for the conversion of alcohols into halides (Cl, Br, I) via the corresponding O-alkyl isoureas
Li, Zhengning,Crosignani, Stefano,Linclau, Bruno
, p. 8143 - 8147 (2007/10/03)
A novel procedure for the conversion of primary and secondary alcohols into the corresponding alkyl chlorides, bromides and iodides is described. The transformation is high-yielding in the case of chlorides and bromides, tolerates a range of functional groups, and does not rely on the use of phosphines.
N-hydroxyurea derivative and pharmaceutical composition containing the same
-
, (2008/06/13)
An N-hydroxyurea derivative having an antiallergic action or anti-inflammatory action having the formula wherein, either one of R1, R3, and R4 represents A, either one of the other groups of R1, R3, and R4 and R2 represents a 3-pyridyl group or 3-pyridylalkyl group, the remaining groups of R1, R2, R3, and R4 independently represent a hydrogen atom, halogen atom, or a substituted or unsubstituted C1 to C8 alkyl group, R5 represents a hydrogen atom or lower alkyl group, R6 represents a hydrogen atom, lower alkyl group, C3 to C7 cycloalkyl group, or a substituted or unsubstituted phenyl group, where the substituent represents a halogen atom, lower alkyl group, or lower alkoxy group, B represents a bond, C1 to C20 alkylene group, C2 to C8 alkenylene group, or C2 to C8 alkynylene group or B—C(R5) represents a C2 to C6 alkylene group having a benzene ring in the middle thereof or its pharmacologically acceptable salt or the hydrate or solvate thereof.
