73208-70-5Relevant articles and documents
Hydride reduction of a lactate ester: Optimisation and scale-up
Donners,Hersmis,Custers,Meuldijk,Vekemans,Hulshof
, p. 606 - 610 (2002)
The two-step synthesis of (2S)-2-(tetrahydropyran-2-yloxy)-propane-1-ol was selected for fine chemical scale-up. The first step, an acid-catalyzed protection of ethyl (S)(-)-lactate with 3,4-dihydro-2H-pyran, could be performed without solvent. The reaction enthalpy was determined to be -48 kJ/mol ethyl (S)-(-)-lactate, ensuring safe scale-up. The crude reaction mixture was used in the second step, the hydride reduction. For the reduction of the protected ester a clear solution of 1 M LiAlH4 in THF was used. The reaction enthalpy was determined to be -313 kJ/mol ethyl (2S)-2-(tetrahydropyran-2-yloxy)propionate, and the work-up was optimised with experimental design techniques. Combination of all experimental and theoretical results resulted in a master recipe for a 10-dm3 scale synthesis of (2S)-2-(tetrahydropyran-2-yloxy)propane-1-ol.
Design and synthesis of paracaseolide a analogues as selective protein tyrosine phosphatase 1B inhibitors
Yin, Jian-Peng,Tang, Chun-Lan,Gao, Li-Xin,Ma, Wei-Ping,Li, Jing-Ya,Li, Ying,Li, Jia,Nan, Fa-Jun
, p. 3441 - 3445 (2014)
A series of structurally related analogues of the natural product paracaseolide A were synthesized and identified as potent PTP1B inhibitors. Among these analogues, compound 10 in particular showed improved PTP1B enzyme inhibitory activity, high selectivity for PTP1B over TC-PTP, and improved cellular effects. the Partner Organisations 2014.
SMALL MOLECULE COMPOUNDS SELECTIVE AGAINST GRAM-NEGATIVE BACTERIAL INFECTIONS
-
Paragraph 0330; 0333; 0334; 0405, (2016/01/30)
The described invention provides fully synthetic, biologically active mangrolide A. It describes schemes to chemically synthesize mangrolide A, intermediates and analogs of mangrolide A, and their antibacterial activity.
Folding of a donor-containing ionene by intercalation with an acceptor
De, Swati,Ramakrishnan
supporting information; experimental part, p. 149 - 156 (2011/10/08)
Cationic ionenes that bear electron-rich 1,5-dialkoxynaphthalene (DAN) units within the alkylene segment were allowed to interact with different types of electron-deficient, acceptor-containing molecules in an effort to realize intercalation-induced folding of the ionenes; the collapse of the chains was expected to occur in such a way that the donor and acceptor units become arranged in an alternating fashion. Several acceptor-bearing molecules were prepared by the derivatization of pyromellitic dianhydride and naphthalene tetracarboxylic dianhydride with two different oligoethylene glycol monomethyl ether monoamines. This yielded acceptor molecules with different water solubility and allowed the examination of solvophobic effects in the folding process. UV/Vis spectroscopic studies were carried out by using a 1:1 mixture of the DAN-ionenes and different acceptor molecules in water/DMSO solvent mixtures. The intensity of the charge-transfer (CT) band was seen to increase with the water content in the solvent mixture, thereby suggesting that the intercalation is indeed aided by solvophobic effects. The naphthalene diimide (NDI) bearing acceptor molecules consistently formed significantly stronger CT complexes when compared to the pyromellitic diimide (PDI) bearing acceptor molecules, which is a reflection of the stronger π-stacking tendency of the former. AFM studies of drop-cast films of different ionene-acceptor combinations revealed that compact folded structures are formed most effectively under conditions in which the strongest CT complex is formed. Know when to fold 'em: When coerced to collapse in a polar solvent in the presence of an electron-deficient amphiphilic folding agent, suitably modified ionenes with a symmetrically positioned electron-rich 1,5-dialkoxylnaphthalene (DAN) unit appear to form an accordion-type folded structure wherein the units are arranged in an alternating fashion (see picture). D=Donor; A=Acceptor. Copyright
