73208-70-5Relevant academic research and scientific papers
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.
Transformation of esters into allyl halides via substituted cyclopropanols. Application in the synthesis of (2S,3R,7R/S)-3,7-dimethyltridec-2-yl acetate and propionate, sex attractants of pine sawfly Diprion pini
Bekish, Andrey V.,Prokhorevich, Konstantin N.,Kulinkovich, Oleg G.
, p. 5253 - 5255 (2004)
A convenient new approach to the synthesis of the acetate and the propionate of (2S,3R,7R/S)-3,7-dimethyltridecan-2-ol, sex attractants of Diprion pini L., using the cyclopropanation of the ethoxycarbonyl group in O-THP protected ethyl (S)-lactate with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide followed by C-2-C-3 cyclopropane ring opening as the key steps has been performed.
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.
Total Synthesis of (+)-Fusarisetin A Driven by a One-Pot Four-Reaction Process
Liu, Chenguang,Zeng, Zhixiong,Chen, Renzhi,Jiang, Xunjin,Wang, Yinglu,Zhang, Yandong
supporting information, p. 624 - 627 (2016/02/18)
A concise, asymmetric total synthesis of (+)-fusarisetin A, a hybrid natural product, has been achieved. A one-pot four-reaction process efficiently delivered the tetracycle 2 which served as a key intermediate for the synthesis of the title natural product and its analogues through amino acid incorporation.
SMALL MOLECULE COMPOUNDS SELECTIVE AGAINST GRAM-NEGATIVE BACTERIAL INFECTIONS
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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.
Total synthesis of lacosamide
Stecko, Sebastian
, p. 6342 - 6346 (2014/07/21)
Total synthesis of anticonvulsant amino acid, lacosamide, is reported. The key step is stereospecific allyl cyanate-to-isocyanate rearrangement, which proceeds with chirality transfer. The enantiopure starting material for the rearrangement step was accessed from ethyl l-lactate.
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
Identification of absolute helical structures of aromatic multilayered oligo(m-phenylurea)s in solution
Kudo, Mayumi,Hanashima, Takayuki,Muranaka, Atsuya,Sato, Hisako,Uchiyama, Masanobu,Azumaya, Isao,Hirano, Tomoya,Kagechika, Hiroyuki,Tanatani, Aya
experimental part, p. 8154 - 8163 (2010/02/28)
(Chemical Equation Presented) The oligomeric aromatic ureas bearing N,N′-dimethylated urea bonds such as 3 have aromatic multi-layered structure, based on the (cis,cis)-urea structure, and also have dynamic helical structure (all-R or all-S axis chirality) when the benzene rings are connected at the meta positions. The absolute helical structure of oligo(m-phenylurea)s were identified by the empirical and theoretical studies on the CD and vibrational CD (VCD) spectra. Thus, each enantiomer of the oligo(m-phenylurea)s 4 bearing a chiral N-2-(methoxyethoxyethoxy)propyl group were synthesized. Intense dispersion-type CD spectra of 4 were observed, which indicated the induction of handedness in the helical structure. In the VCD spectra of 4 in the film state, the signals due to the carbonyl and aromatic ring vibrations were seen with negative and positive values for compounds 4a and 4b, respectively. The calculations of both CD and VCD spectra of oligo(m-phenylurea)s 3 without any chiral N-substituent gave the same assignment about the axis chirality of 4. Thus, the absolute configurations of 4a and 4b are all-R and all-S structures, respectively. 2009 American Chemical Society.
Synthesis of the active form of loxoprofen by using allylic substitutions in two steps
Hyodo, Tomonori,Kiyotsuka, Yohei,Kobayashi, Yuichi
supporting information; experimental part, p. 1103 - 1106 (2009/07/25)
High regioselectivity for allylic substitution of the cyclopentenyl picolinate 5 with benzylcopper reagent was attained with ZnBr2, and the finding was applied to the p-BrC6H4CH2 reagent. The cyclopentene moiety in the product was reduced to the cyclopentane, and the p-BrC6H4 was converted to the "Cu"C6H4 for the second allylic substitution with picolinate 8 to furnish the title compound after oxidative cleavage of the resulting olefin moiety.
A male-produced aggregation pheromone blend consisting of alkanediols, terpenoids, and an aromatic alcohol from the cerambycid beetle Megacyllene caryae
Lacey, Emerson S.,Moreira, Jardel A.,Millar, Jocelyn G.,Hanks, Lawrence M.
, p. 408 - 417 (2008/09/18)
Bioassays conducted with a Y-tube olfactometer provided evidence that both sexes of the cerambycid beetle Megacyllene caryae (Gahan) were attracted to odor produced by males. Odor collected from male M. caryae contained eight male-specific compounds: a 10:1 blend of (2S,3R)- and (2R,3S)-2,3-hexanediols (representing 3.2±1.3% of the total male-specific compounds), (S)-(-)-limonene (3.1±1.7%), 2-phenylethanol (8.0±2.4%), (-)-α-terpineol (10.0±2.8%), nerol (2.1±1.5%), neral (63.3±7.3%), and geranial (8.8±2.4%). Initial field bioassays determined that none of these compounds was attractive as a single component. Further field trials that used a subtractive bioassay strategy determined that both sexes were attracted to the complete blend of synthetic components, but the elimination of any one component resulted in a decline in trap captures. Blends that were missing (2S,3R)-2,3-hexanediol, (2R,3S)-2,3-hexanediol, or citral (a 1:1 mixture of neral and geranial) attracted no more beetles than did controls. A pheromone blend of this complexity, composed of alkanediols, terpenoids, and aromatic alcohols, is unprecedented for cerambycid species.
