112968-75-9Relevant articles and documents
Origin of Chiral Induction in Radical Reactions with the Diastereoisomers (5R)- and (5S)-5-l-Menthyloxyfuran-2[5H]-one
Marinkovic, Sinisa,Brule, Cedric,Hoffmann, Norbert,Prost, Elise,Nuzillard, Jean-Marc,Bulach, Veronique
, p. 1646 - 1651 (2004)
Acetalization of 5-hydroxyfuran-2[5H]-one with l-menthol yields (5R)-(1) and (5S)-5-l-menthyloxyfuran-2[5H]-one (2) in equal amounts. The diastereomer 1 crystallizes preferentially. For the first time, the isolation of pure diastereoisomer 2 is reported. Different diastereoselectivities were observed in the radical tandem reaction of 1 and 2 with N,N-dimethylaniline. The privileged conformations in solution of the substrates and the products of the radical reaction were then determined, and X-ray crystal structure analyses were carried out on the reaction products. The different stereoselectivities in both cases are explained by different orientations of the menthyloxy substituent.
Studies on the chemistry of the chiral nitronic acid and nitronic esters
Kang, Fu-An,Yin, Cheng-Lie
, p. 3585 - 3589 (1997)
Some new chemistry of the chiral nitronic acid and nitronic esters is described. Conversions with retention of configuration are found among the chiral nitronic acid, oxime, nitronic esters and O-alkyloximes. α,β- Elimination reactions of nitronic esters are observed for the first time. Novel and enantiopure chiral bisheterocyclic compounds are obtained via highly diastereoselective 1,3-dipolar cycloaddition of the chiral nitronic esters with ethyl acrylate.
Four Stereoisomers of 2-Aminomethyl-1-cyclopropanecarboxylic Acid: Synthesis and biological evaluation
Oikawa, Masato,Sugeno, Yuka,Tukada, Hideyuki,Takasaki, Yuichi,Takamizawa, Satoshi,Irie, Raku
supporting information, p. 1816 - 1823 (2019/11/13)
Here, we report a practical method for asymmetric synthesis of cyclopropane-fused GABA analogs. Starting from 2-furaldehyde, the cis-isomer (CAMP) was synthesized over 10 steps; (1)- and (+)-CAMP￠HCl were synthesized by employing d- and l-menth
Highly enantioselective synthesis and potential biological activity of chiral novel nucleoside analogues containing adenine and naturally phenol derivatives
He, Lan,Liu, Yumei,Zhang, Wei,Li, Ming,Chen, Qinghua
, p. 8505 - 8511 (2007/10/03)
This paper described an efficient synthetic strategy for chiral acyclic nucleoside analogues containing both the phenoxy components of some bioactive natural compounds and a heterocyclic base. The phenoxy components with adenine moiety were incorporated into the chiral acyclic nucleoside analogues through two key synthetic tactics. Chiron 5-(R)-menthyloxy-2(5H)-furanone 5 was obtained in good yield from the cheap starting material furfural via a valuable synthetic route. The asymmetric Michael addition of 5 with adenine and the subsequent reduction reaction afforded the key chiral intermediate, 2-(R)-(9′-adeninyl)-1,4-butanediol 8. The absolute configuration of 8 was established by X-ray crystallography. The intermolecular dehydration reaction between 2-(9′-adeninyl)-1,4-butanediol 8 and phenoxy components 9 on treatment with diethyl azodicarboxylate and triphenylphosphine was carried out to give the chiral acyclic nucleoside analogues 1a-1e. The regioselectivity of the reaction was established by NMR methods, especially through 13C NMR shifts and NOE effect observed in the target molecule 1c, as well as by HMBC/HMQC experiments. The target compounds were tested for inhibition of cytopathogenicity against different cancer cells and exhibited potential anticancer activity.
