99165-40-9Relevant academic research and scientific papers
Electrochemical methoxymethylation of alcohols-a new, green and safe approach for the preparation of MOM ethers and other acetals
Luo, Xiya,Ma, Xiaofeng,Lebreux, Frédéric,Markó, István E.,Lam, Kevin
supporting information, p. 9969 - 9972 (2018/09/11)
A new, green, safe, cost-effective and highly efficient electrochemical approach for the methoxymethylation of alcohols and phenols was successfully developed. The methodology was also applied to the synthesis of substituted acetals.
A Migratory Ether Formation Route to Medium-Sized Sugar Mimetics
Jiang, Hao,Xu, Li-Ping,Fang, Yan,Zhang, Zhen-Xing,Yang, Zhen,Huang, Yong
supporting information, p. 14340 - 14344 (2016/11/11)
Polyol-substituted cyclic ethers are fundamental building blocks of biomolecules. The position and stereochemistry of multiple hydroxy substituents of cyclic ethers play a central role in their biological function. Current methods for the synthesis of such structures are limited to “naked” ring products with no or few substituents. Here we describe a general route to medium-sized polyol cyclic ethers using a migratory ether formation strategy. In contrast to the common pathway of direct opening of epoxides, Me3Al was found to promote an unprecedented ether addition reaction, opening a neighboring epoxide. The resulting oxonium intermediate triggers a 1,3-methyl shift to yield 2-deoxyribital products. When the hemiacetal auxiliary is a monosaccharide, the sugar ring is expanded by four atoms to give the corresponding 9- to 11-membered analogues. This method provides an entry into the untapped chemical space of medium-sized sugar mimetics.
The "Aqueous" Prins Reaction
Aubele, Danielle L.,Lee, Christopher A.,Floreancig, Paul E.
, p. 4521 - 4523 (2007/10/03)
(Equation presented) In this communication we demonstrate that Prins cyclization reactions occur under very mild conditions when cyclic α,β-unsaturated acetals are employed as oxocarbenium ion progenitors and allylsilanes are used as nucleophiles. Cycliza
Quaternary salts of 2-[(hydroxyimino)methyl]imidazole. 3. Synthesis and evaluation of (alkenyloxy)-, (alkynyloxy)-, and (aralkyloxy)methyl quaternarized 2[(hydroxyimino)methyl]-1-alkylimidazolium halides as reactivators and therapy for soman intoxication
Bedford,Harris III,Howd,Goff,Koolpe,Petesch,Koplovitz,Sultan,Musallam
, p. 504 - 516 (2007/10/02)
A series of structurally related monosubstituted 1-[(alkenyloxy)methyl]-, 1-[(alkynyloxy)methyl]-, and 1-[(aralkyloxy)methyl]-2-[(hydroxyimino)methyl]-3-methylimidazolium halides were prepared and evaluated. All new compounds were characterized with respect to (hydroxyimino)methyl acid dissocation constant, nucleophilicity, and octanol-buffer partition coefficient. The alkynyloxy-substituted compounds were also evaluated in vitro with respect to reversible inhibition of human erythrocyte (RBC) acetylcholinesterase (AChE) and kinetics of reactivation of human AChE inhibited by ethyl p-nitrophenyl methylphosphonate (EPMP). In vivo evaluation in mice revealed that coadministration of alkynyloxy-substituted imidazolium compounds with atropine sulfate provided significant protection against a 2 x LD50 challenge of GD. For the alkynyloxy-substituted imidazolium drugs there is a direct relationship between in vitro and in vivo activity: the most potent in vivo compounds against GD proved to be potent in vitro reactivators against EPMP-inhibited human AChE. These results differ from the observations made on the sterically hindered imidazolium compounds (see previous article) and suggest that several antidotal mechanisms of protective action may be applicable for the imidazolium aldoxime family of therapeutics. The ability of the alkynyloxy substituents to provide life-saving protection against GD intoxication was not transferable to the pyridinium or triazolium heteroaromatic ring systems.
