54868-49-4Relevant academic research and scientific papers
The synthesis and biological characterization of a ceramide library
Chang, Young-Tae,Choi, Jaehwa,Ding, Sheng,Prieschl, Eva E.,Baumruker, Thomas,Lee, Jae-Mok,Chung, Sung-Kee,Schultz, Peter G.
, p. 1856 - 1857 (2007/10/03)
A facile synthesis of a combinatorial ceramide library and their activities in the NF-κB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-κB activating molecule was discovered among ceramide containing β-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated. Copyright
Iodocyclofunctionalization of (Z)-1-Trichloroacetimidoyloxyalk-2-enes and 3-Trichloroacetimidoyloxyalk-1-enes. Synthesis of (+/-)-erythro-Sphinganine Triacetate and (+/-)-threo-Sphinganine Triacetate
Bongini, Alessandro,Cardillo, Giuliana,Orena, Mario,Sandri, Sergio,Tomasini, Claudia
, p. 1339 - 1344 (2007/10/02)
(Z)-1-Trichloroacetimidoyloxyoctadec-2-ene, easily obtained from (Z)-octadec-2-en-1-ol, was iodocyclized with N-iodosuccinimide to give the 4-(1-iodohexadecyl)-2-trichloromethyl-4,5-dihidro-oxazole.From this compound, two routes were developed, either to pure (+/-)-erythro-sphinganine triacetate or to pure (+/-)-threo-sphinganine triacetate, respectively.The neutral cleavage of 4-(1-iodohexadecyl)-2-trichloromethyl-4,5,-dihydro-oxazole gave the corresponding amide which, by treatment with Amberlyst A 26 (CO3(2-) form), afforded the cis-4-hydroxymethyl-5-pentadecyl-2-trichloromethyl-4,5-dihydro-oxazole together with a minor amount of cis-2-hydroxymethyl-3-pentadecylaziridine.After hydrolysis of the oxazole and full acetylation, (+/-)-erythro-sphinganine triacetate was obtained in 70 percent yield.On the other hand, acidic cleavage of the 4-(1-iodohexadecyl)oxazole 2-amino-3-iodo-octadecan-1-ol hydrochloride, which was directly treated with Amberlyst A 26 (AcO(-) form).The product was acetylated and (+/-)-threo-sphinganine triacetate was recovered in 70 percent yield after chromatographic separation.As an alternative, 3-trichloroacetimidoyloxyoctadec-1-ene was cyclized with N-iodosuccinimide to give a 20:80 cis:trans mixture of 4-iodomethyl-5-pentadecyl-2-trichloromethyl-4,5-dihydro-oxazoles.After ring cleavage, the corresponding ring-opened hydrochlorides were obtained.The mixture was then treated with Amberlyst A 26 (AcO(-) form) and the product was directly acetylated.After silica gel chromatography, (+/-)-threo-sphinganine triacetate and (+/-)-erithro-sphinganine triacete were obtained in good yield, in the ratio 80:20.
Iodocyclofunctionalization of (E)-1-Trichloroacetimidoalk-2-enes. Synthesis of (+/-)-erythro-Sphinganine Triacetate
Bongini, Alessandro,Cardillo, Giuliana,Orena, Mario,Sandri, Sergio,Tomasini, Claudia
, p. 1345 - 1350 (2007/10/02)
From the iodocyclization of (E)-1-trichloroacetimido-octadec-2-ene, 5-iodo-4-pentadecyl-2-trichloromethyl-5,6-dihydro-4H-oxazine was unexpectedly obtained, whose structue was assigned from i.r. and (1)H n.m.r. spectra.The stereostructure of this oxazine was further confirmed by chemical evidence: thus, the compound was hydrolysed on silica gel to give 2-iodo-3-trichloroacetimido-octadecan-1-ol, and successive treatment with Amberlyst A 26 (CO3(2-) form) yielded cis-5-hydroxymethyl-4-pentadecyl-4,5-dihydro-oxazole, whose configuration was determined by (1)H n.m.r. data.Acidic hydrolysis of this oxazole and acetylation led to erythro-3-aminno-octadecane-1,2-diol triacetate.To ascertain definitively the structure of this triacetate, 3-trichloroacetamido-octadec-1-ene was cyclized, to yield 5-iodomethyl-4-pentadecyl-4,5-dihydro-oxazole as a 45:55 cis:trans mixture.After hydrolysis of the cis-isomer, treatment with Amberlyst A 26 (AcO(1-) form), and full acetylation, the aforementioned erythro-triacetate was obtained.Confirming the unequivocal assignment of the stereostructure of 5-iodo-4-pentadecyl-2-trichloromethyl-5,6-dihydro-4H-oxazine, its acidic cleavage gave 3-amino-1-iodo-octadecan-2-ol hydrochloride.By treatment of this salt with Amberlyst A 26 (AcO(1-) form), full acetylation of the product afforded (+/-)-erythro-sphinganine triacetate in good yield, contaminated with a minor amount of the regioisomeric 3-amino-octadecanediol-triacetate.
