82741-59-1Relevant academic research and scientific papers
First syntheses of model long-chain trichloro[ω-(trimethylsilyl)alkynyl]silanes suitable for self-assembled monolayers on silicon surfaces
Banaszak, Estelle,Xu, Li-Wen,Bardeau, Jean-Fran?ois,Castanet, Anne-Sophie,Mortier, Jacques
, p. 3961 - 3966 (2009)
The preparation of the title compounds involves the introduction of the required Me3SiC{triple bond, long}C and trichlorosilyl groups at the termini of the alkyl chain via derivatization of easily accessible and inexpensive materials/reagents. Trichloro[ω-(trimethylsilyl)alkynyl]silanes are useful for the linkage to a hydroxylated silicon surface for multilayer formation and for further chemical modification of the tail group of the monolayer.
Scalable Synthesis of Human Ultralong Chain Ceramides
Opálka, Luká?,Ková?ik, Andrej,Sochorová, Michaela,Roh, Jaroslav,Kune?, Ji?í,Len?o, Juraj,Vávrová, Kate?ina
supporting information, p. 5456 - 5459 (2015/11/18)
Ceramides with ultralong chains (≥30 carbons), also known as acylceramides, play a critical role in the survival of mammals on dry land. An efficient and scalable synthesis of four major classes of ultralong human skin ceramides is reported. The key approach involves the use of a succinimidyl ester that acts as a protective group, helps overcome the extremely low solubility, and simultaneously activates the fatty acid for its clean and high-yielding attachment to a sphingoid base.
Pachychalines A-C: Novel 3-alkylpyridinium salts from the marine sponge Pachychalina sp.
Laville, Remi,Thomas, Olivier P.,Berrue, Fabrice,Reyes, Fernando,Amade, Philippe
, p. 121 - 125 (2008/09/17)
Three 3-alkylpyridinium salts, pachychalines A (1), B (2) and C (3), were isolated from the Caribbean marine sponge Pachychalina sp. (order Haplosclerida). They are the first examples of 3-(aminoalkyl)pyridinium salts. Their chemical structures were elucidated by NMR spectroscopy and detailed ESI HRMS-MS analysis. The total synthesis of 1 allowed the confirmation of the unusual C-C connection between both pyridinium moieties. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
General synthesis and aggregation behaviour of a series of single-chain 1,ω-Bis(phosphocholines)
Drescher, Simon,Meister, Annette,Blume, Alfred,Karlsson, Goeran,Almgren, Mats,Dobner, Bodo
, p. 5300 - 5307 (2008/02/11)
The synthesis and physicochemical characterisation of a series of polymethylene-1,ω-bis(phosphocholines) with even-numbered chain lengths between 22 and 32 carbon atoms is described. Two new synthetic strategies for the preparation of long-chain 1,ω-diols as hydrocarbon building blocks are presented. The temperature-dependent self-assembly of the single-chain bolaamphiphiles was investigated by cryo transmission electron microscopy (cryo-TEM), differential scanning calorimetry (DSC), and Fourier transform infrared spectroscopy (FTIR).
Total Synthesis of Naturally Occurring Mycolic Acids. (E)- and (Z)-threo-2-Docosyl-3-hydroxytetracont-21-enoate
Huang, Harry C.,Rehmann, Jill K.,Gray, Gary R.
, p. 4018 - 4023 (2007/10/02)
The ethyl esters of (E)- and (Z)-2-docosyl-3-hydroxytetracont-21-enoate (4a and 4b, respectively) have been prepared by a route involving alkylation of the dianion of ethyl 2-docosyl-3-oxobutyrate (2) with either (E)-1-iodo-17-hexatriacontene (14c) or (Z)-1-iodo-17-hexatriacontene (13c) and subsequent borohydride reduction of the intermediate β-keto esters (3a and 3b, respectively).Resolution of the 3:2 mixture of erythro and threo diastereomers of 4a and 4b was accomplished by high-performance liquid chromatography, employing phenacyl ester derivatives.The 1H NMR spectra of phenacyl (E)-threo-2-docosyl-3-hydroxytetracont-21-enoate (6a) and phenacyl (Z)-threo-2-docosyl-3-hydroxytetracont-21-enoate (6b) were identical with the spectra previously reported for the phenacyl esters of the naturally occurring monoalkene mycolic acids from Mycobacterium smegmatis (see ref 10).An examination of the phenacyl ester of the epoxide derivative of the naturally occurring mycolic acid by 1H NMR spectroscopy established that it was a 93:7 mixture of the Z and E isomers, respectively, of phenacyl threo-2-docosyl-3-hydroxytetracont-21-enoate.
