33106-32-0Relevant academic research and scientific papers
HPLC separation of 2-aryloxycarboxylic acid enantiomers on chiral stationary phases
Charushin, V. N.,Chulakov, E. N.,Krasnov, V. P.,Levit, G. L.,Sadretdinova, L. Sh.,Tumashov, A. A.,Vakarov, S. A.
, p. 900 - 907 (2021/06/07)
The possibility for separating enantiomers of a number of practically significant 2-aryloxycarboxylic acids was studied by normal- and reversed-phase HPLC on popular chiral stationary phases. The best separation parameters were achieved on the chiral phases with the polysaccharide base Chiralcel OD-H and Chiralpack AD under the normal-phase HPLC conditions. The (S)- and (R)-enantiomers of 2-(1-naphthyloxy)- and 2-(2-iodophenoxy)propionic acids with enantiomeric excess ee >99% were isolated using preparative chiral HPLC.
De novo synthesis of novel bacterial monosaccharide fusaminic acid
Wei, Ruohan,Liu, Han,Li, Xuechen
, p. 420 - 431 (2019/03/29)
Fusobacterium nucleatum is an oral bacteria related to various types of diseases. As Gram-negative bacteria, lipopolysaccharide (LPS) of Fusobacterium nucleatum could be a potential virulence factor. Recently, the structure of O-antigen in LPS of Fusobact
Stereodivergence in the Ireland-Claisen Rearrangement of α-Alkoxy Esters
Podunavac, Ma?a,Lacharity, Jacob J.,Jones, Kerry E.,Zakarian, Armen
supporting information, p. 4867 - 4870 (2018/08/24)
A systematic investigation into the Ireland-Claisen rearrangement of α-alkoxy esters is reported. In all cases, the use of KN(SiMe3)2 in toluene gave rearrangement products corresponding to a Z-enolate intermediate with excellent diastereoselectivity, presumably because of chelation control. On the other hand, chelation-controlled enolate formation could be overcome for most substrates through the use of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).
Total synthesis and biological activity of dolastatin 16
Casalme, Loida O.,Yamauchi, Arisa,Sato, Akinori,Petitbois, Julie G.,Nogata, Yasuyuki,Yoshimura, Erina,Okino, Tatsufumi,Umezawa, Taiki,Matsuda, Fuyuhiko
supporting information, p. 1140 - 1150 (2017/02/10)
The total synthesis of dolastatin 16, a macrocyclic depsipeptide first isolated from the sea hare Dolabella auricularia as a potential antineoplastic metabolite by Pettit et al., was achieved in a convergent manner. Dolastatin 16 was reported by Tan to ex
Acyclic 1,4-Stereocontrol via the Allylic Diazene Rearrangement: Development, Applications, and the Essential Role of Kinetic e Stereoselectivity in Tosylhydrazone Formation
Shrestha, Maha L.,Qi, Wei,McIntosh, Matthias C.
, p. 8359 - 8370 (2017/08/23)
We report full details of a method for 1,3-reductive transposition of α-alkoxy-α,β-unsaturated hydrazones to provide E-alkenes with high 1,4-stereocontrol between the two respective allylic stereocenters. The process couples a chelation-controlled reduction of the hydrazone with an in situ allylic strain controlled retro-ene reaction of an allyl diazene, i.e., an allylic diazene rearrangement. Such stereotriads are frequently observed motifs in natural products. We observed a fortuitous kinetic preference for the E-hydrazone geometry during the hydrazonation reaction, as only the E-isomers could undergo chelation-controlled reduction.
COMPOUNDS FOR USE IN TREATING NEUROMUSCULAR DISORDERS
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Page/Page column 103; 104, (2017/01/02)
The present invention relates to compositions comprising compounds for use in treating, ameliorating and/or preventing neuromuscular disorders. The compounds as defined herein preferably inhibit the ClC-1 ion channel. The invention further relates to methods of treating, preventing and/or ameliorating neuromuscular disorders, by administering said composition to a person in need thereof.
Ultrashort helix pitch antiferroelectric liquid crystals based on chiral esters of terphenyldicarboxylic acid
Pozhidaev,Vashchenko,Mikhailenko,Krivoshey,Barbashov,Shi,Srivastava,Chigrinov,Kwok
supporting information, p. 10339 - 10346 (2016/11/17)
Antiferroelectric liquid crystals (AFLCs) with a nanoscale helix pitch (100 nm) were revealed in a composition containing achiral smectic-C biphenylpyrimidines and two non-mesogenic chiral dopants: p-terphenyldicarboxylates of chiral (2S)-1,1,1-trifluorooctane-2-ol and (S,S)-1,1,1-trifluorooctan-2-yl 2-hydroxypropanoate. The prepared multicomponent AFLCs exhibit two electro-optical effects, which are interrelated with the chemical structures of the mixture's components. The first effect is hysteresis free under special voltage waveform U-shaped switching, which exhibits an electro-optical response similar to that of nematic liquid crystals (NLCs) but around 1-2 orders of magnitude faster. Secondly, the deformed helix antiferroelectric liquid crystal (DHAFLC) effect has been investigated. The observed temperature independence of the electro-optical parameters, in a certain temperature range, combined with a fast U-shape response or with DHAFLC, adds a great value for applications.
Antineoplastic agents. 599. Total synthesis of dolastatin 16
Pettit, George R.,Smith, Thomas H.,Arce, Pablo M.,Flahive, Erik J.,Anderson, Collin R.,Chapuis, Jean-Charles,Xu, Jun-Ping,Groy, Thomas L.,Belcher, Paul E.,Macdonald, Christian B.
, p. 476 - 485 (2015/04/14)
The first 23-step total synthesis of the cyclodepsipeptide dolastatin 16 (1) has been achieved. Synthesis of the dolaphenvaline and dolamethylleuine amino acid units using simplified methods improved the overall efficiency. The formation of the 25-membere
Developing Pd(II) catalyzed double sp3 C-H alkoxylation for synthesis of symmetric and unsymmetric acetals
Zong, Yu,Rao, Yu
supporting information, p. 5278 - 5281 (2015/01/09)
An effective Pd(II) catalyzed double unactivated C(sp3)-H alkoxylation has been developed to prepare both symmetric and unsymmetric acetals. This new reaction demonstrates good functional group tolerance, excellent reactivity, and high yields. A variety of novel acetals can be readily accessed via this new method. (Chemical Equation Presented).
Catalytic enantioselective inverse electron demand hetero-diels-alder reaction with allylsilanes
Matsumura, Yuki,Suzuki, Takahiro,Sakakura, Akira,Ishihara, Kazuaki
, p. 6131 - 6134 (2014/06/23)
The first diastereo- and enantioselective inverse electron demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketoesters with allylsilanes is described. Chiral copper(II) catalysts successfully activate the β,γ-unsaturated α-ketoesters and promote the reaction with allylsilanes with excellent enantioselectivities. This process represents a new entry to chiral oxanes.
