92077-90-2Relevant academic research and scientific papers
An (S)-(+)-Lactic Acid Route to (2S,6R,8S)-2,8-Dimethyl-1,7-dioxaspiroundecane and (2S,6R,8S)-2-Ethyl-8-methyl-1,7-dioxaspiroundecane and Demonstration of their Presence in the Rectal Glandular Secretion of Bactrocera nigrotibialis (Perkin)
Perkins, Michael V.,Kitching, William,Koenig, Wilfried A.,Drew, Richard A. I.
, p. 2501 - 2506 (1990)
The chiral iodide resulting from reduction and iodination of the tetrahydropyran-2-yl ether of ethyl (S)-(+)-lactate has been engaged in a free-radical addition to acrylonitrile.The resulting protected hydroxy nitrile, on reaction with pent-4-enylmagnesium bromide afforded (S)-2-tetrahydropyran-2-yloxyundec-10-en-6-one.Oxymercuration of this hydroxy enone, under reversible conditions, employing aqueous acid-tetrahydrofuran, effected simultaneous deprotection and cyclisation, and in situ biphasic demercuration with sodium borohydride provided essentially stereochemically pure (2S,6R,8S)-2,8-dimethyl-1,7-dioxaspiroundecane .Epoxidation of the protected hydroxy enone, followed by dimethylcuprate ring-opening and cyclisation, provided a mixture of the (E,E) and the two possible (E,Z)-diastereomers of 2-ethyl-8-methyl-1,7-dioxaspiroundecane with the former being the (2S,6R,8S) stereoisomer.Separation of the (E,E) from the two (E,Z) isomers was achieved by preparative gas chromatography.GC analysis of these samples and of the rectal glandular secretion of male Bactrocera nigrobialis, using a cyclodextrin-based phase, demonstrated that (2S,6R,8S)-stereoisomers of the 2,8-dimethyl-and 2-ethyl-8-methyl-1,7-dioxaspiroundecanes were the natural products, with no detectable level of the antipodes.
New Symmetrical Chiral Dibenzyl- and Diphenyl-Substituted Diamido-, Dithionoamido-, Diaza-, and Azapyridino-18-crown-6 Ligands
Huszthy, Peter,Oue, Masatoshi,Bradshaw, Jerald S.,Zhu, Cheng Y.,Wang, Tingmin,et al.
, p. 5383 - 5394 (2007/10/02)
Eleven new chiral macrocycles (1-11, see Figure 1) of the pyridino-18-crown-6 type have been prepared.Nine diazapyridino-crown ligands contain two amide (1, R = benzyl; 4, R = phenyl), two N-methylamide (7, R = phenyl), two thionoamide (2, R = benzyl; 5,
Synthesis and Mesomorphic Properties of 4-Substituted Phenyl and Phenylthio-4'--Benzoates
Neubert, M. E.,Sabol-Keast, S.
, p. 67 - 74 (2007/10/02)
A variety of esters and thioesters of the type were prepared by esterification of the acid with the phenols and thiols using the carbodiimide method.These compounds were of interest as possible ferroelectric liquid crystals.The required acid was
