- New amphiphilic polycarbonates with side functionalized cholesteryl groups as biomesogenic units: synthesis, structure and liquid crystal behavior
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The synthesis of four new amphipathic copolymers with side functionalized-cholesterol based aliphatic polycarbonates is described through the ring-opening polymerization and coupling reaction. The chemical structures, liquid crystal (LC) behavior, and thermal stability of the chiral monomers and copolymers obtained in this study were characterized using Fourier transform infrared (FT-IR) spectroscopy, proton nuclear magnetic resonance (1H NMR) spectroscopy, gel permeation chromatography (GPC), polarizing optical microscopy (POM), differential scanning calorimetry (DSC), X-ray diffraction (XRD), and thermogravimetric analysis (TGA) measurements. The effect of the spacer length on the molecular interaction and mesophase of the chiral monomers and copolymers was investigated. It was found that chiral monomers with longer spacer seemed beneficial for the formation of mesophases, and the additional ordering on polymerization caused mesophases to be more ordered than for the corresponding monomers. The LC copolymers all revealed a smectic A phase with an interdigitated molecular arrangement. The results seemed to show a decreased tendency toward the glass transition temperature, and isotropic temperature for the LC copolymers by increasing the spacer length. In addition, four LC copolymers had a good thermal stability.
- Xu, Xiaoxu,Liu, Xiaofeng,Li, Qun,Hu, Jianshe,Chen, Qifan,Yang, Liqun,Lu, Yanhua
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Read Online
- Polycarbonate and poly(carbonate-ester)s synthesized from biocompatible building blocks of glycerol and lactic acid
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The synthesis and characterization of a polycarbonate of glycerol and poly(carbonate-ester)s of glycerol and L-lactic acid are reported. These new polymers possess a hydrolyzable backbone, tunable hydrophobic/hydrophilic properties, and functionalizable p
- Ray III, William C.,Grinstaff, Mark W.
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Read Online
- BORON CLUSTER-COUPLED COMPOUND
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To provide a novel boron-containing compound which increases intratumorous accumulation and tumor retention, and is efficiently taken into a tumor cell.SOLUTION: The present invention relates to a compound represented by formula (I) in the figure or a salt thereof. [In the formula, X represents a divalent to pentavalent organic group; Y represents a linker structure; R represents a monovalent group comprising boron clusters; and n represents 2, 3, 4 or 5.SELECTED DRAWING: None
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Paragraph 0178; 0186-0188
(2021/03/05)
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- Synthesis and catalytic evaluation of acidic carbons in the etherification of glycerol obtained from biodiesel production
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In this paper, the catalytic behaviour of carbonaceous system (Ccs) functionalized with –SO3H groups were studied in the etherification of refined (Gly) and crude glycerol (GlyC), with benzyl alcohol (BA). This Ccs was obtained by a synthetic method with low energetic cost in only 24 h. Its catalytic activity and selectivity were studied varying the catalyst percentage (2.5, 5 and 10 wt.%), the initial reactant molar ratio and temperature (between 80 and 120 °C). A very good catalytic performance was achieved (97 % conversion after 360 min of reaction), at 120 °C, Gly:BA = 3:1 and 10 wt.% of Ccs. The high activity can be attributed to high acid site density (6.4 mmol H+/g), that also allowed us to working at lower reaction temperature (100 °C) and with less catalyst concentration (2.5 wt.%), without observing significant loss in BA conversion. Monoether (ME1) was the major product of the reaction with 72 % selectivity. The material can be reused and still gives a notable conversion of BA (about 43 %) after three successive reuses. Finally, the Ccs was active and selective to the desired products in the etherification of crude glycerol (GlyC) derived of biodiesel industry. An important BA conversion (45 %) was obtained only reducing the water content of GlyC and without carrying out any other purification and/or neutralization treatment.
- Chiosso, María E.,Casella, Mónica L.,Merlo, Andrea B.
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p. 107 - 114
(2020/10/29)
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- Glycerol conversion to high-value chemicals: The implication of unnatural α-amino acid syntheses using natural resources
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Glycerol derivatives are an important class of compounds, which have great applications as basic structural building blocks in organic synthesis. O-Benzylglycerol was oxidised to produce a high-value compound in high yield using a NaOtBu-O2 system. Furthermore, the synthetic utility of the resulting product was demonstrated by its transformation into unnatural α-amino acids, thus showing the valorisation of glycerol biomass.
- Park, Yun Ji,Yang, Jung Woon
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supporting information
p. 2615 - 2620
(2019/06/03)
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- Regioselective Ring-Opening of Glycidol to Monoalkyl Glyceryl Ethers Promoted by an [OSSO]-FeIII Triflate Complex
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A FeIII-triflate complex, bearing a bis-thioether-di-phenolate [OSSO]-type ligand, was discovered to promote the ring-opening of glycidol with alcohols under mild reaction conditions (0.05 mol % catalyst and 80 °C). The reaction proceeded with high activity (initial turnover frequency of 1680 h?1 for EtOH) and selectivity (>95 %) toward the formation of twelve monoalkyl glyceryl ethers (MAGEs) in a regioselective fashion (84–96 % yield of the non-symmetric regioisomer). This synthetic approach allows the conversion of a glycerol-derived platform molecule (i.e., glycidol) to high-value-added products by using an Earth-crust abundant metal-based catalyst.
- Monica, Francesco Della,Ricciardi, Maria,Proto, Antonio,Cucciniello, Raffaele,Capacchione, Carmine
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p. 3448 - 3452
(2019/08/01)
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- COMPOSITIONS AND METHODS FOR THE TREATMENT OF UREA CYCLE DISORDERS AND HEPATIC DISEASES
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The compositions and compounds of formula I, formula II, formula III which includes a molecular conjugate with ornithine or its polymorphs, enantiomers, stereoisomers, solvates, and hydrates thereof. These salts may be formulated as pharmaceutical composi
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Paragraph 00154
(2017/06/20)
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- TYK2 INHIBITORS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.
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Paragraph 00875
(2017/03/21)
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- Synthesis and evaluation of symmetric acyclic nucleoside bisphosphonates as inhibitors of the Plasmodium falciparum, Plasmodium vivax and human 6-oxopurine phosphoribosyltransferases and the antimalarial activity of their prodrugs
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Two new series of symmetric acyclic nucleoside bisphosphonates (ANbPs) have been synthesised as potential inhibitors of the Plasmodium falciparum (Pf) and vivax (Pv) 6-oxopurine phosphoribosyltransferases. The structural variability between these symmetric ANbPs lies in the number of atoms in the two acyclic linkers connecting the N9 atom of the purine base to each of two phosphonate groups and the branching point of the acyclic moiety relative to the purine base, which occurs at either the alpha or beta positions. Within each series, six different 6-oxopurine bases have been attached. In general, the ANbPs with either guanine or hypoxanthine have lower Ki values than for those containing either the 8-bromo or 7-deaza 6-oxopurine bases. The lowest Ki values obtained for the two parasite enzymes were 0.1?μM (Pf) and 0.2?μM (Pv) for this series of compounds. Two phosphoramidate prodrugs of these inhibitors exhibited antimalarial activity against Pf in infected erythrocyte cell culture with IC50 values of 0.8 and 1.5?μM. These two compounds exhibited low cytotoxicity in human A549 cells having CC50 values of >300?μM resulting in an excellent selectivity index.
- ?pa?ek, Petr,Keough, Dianne T.,Chavchich, Marina,Dra?ínsky, Martin,Janeba, Zlatko,Naesens, Lieve,Edstein, Michael D.,Guddat, Luke W.,Hocková, Dana
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p. 4008 - 4030
(2017/07/05)
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- Dual-Targeted Cascade-Responsive Prodrug Micelle System for Tumor Therapy in Vivo
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This study reports a cascade-responsive disassemble micellar drug delivery system with dual-targeting potential (cell and mitochondria targeting), which optimizes the distribution of antitumor drugs on systemic, local, and subcellular levels to enhance antitumor efficacy. A new cationic porphyrin derivative 5-(3-hydroxy-p-(4-trimethylammonium)butoxyphenyl)-10,15,20-triphenylporphyrin chlorine (MTPP) is synthesized as a mitochondria-targeting photosensitizer. After accumulating at a tumor site, the micellar nanosystem is endocytosed by tumor cells facilitated by the folate receptor-mediated pathway. Then, the hydrophobic PDEA block would be protonated in intracellular acidic endo-/lysosomes and promote the escape of prodrug micelles from endo-/lysosome to cytoplasm, resulting in the first-stage destabilization of micelles. Subsequently, the CPT is released in response to high concentration of GSH in cytoplasm, which would greatly increase the hydrophilicity of the BOH block and initiate the complete disassembly of the polymer micelles owing to the damage of the hydrophilic-hydrophobic balance. Additionally, the released MTPP is selectively accumulated in mitochondria and activates mitochondria apoptotic pathway upon light irradiation as a result of ROS generation. Both in vitro and in vivo studies indicate that the polymeric micelle not only effectively improves the targeted delivery efficiency but also dramatically enhances the combinational antitumor efficacy while reducing the side effects associated with the laser irradiation and mitochondria-targeted tumor therapy.
- Dai, Liangliang,Cai, Ruisi,Li, Menghuan,Luo, Zhong,Yu, Yonglin,Chen, Weizhen,Shen, Xinkun,Pei, Yuxia,Zhao, Xiaojing,Cai, Kaiyong
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p. 6976 - 6992
(2017/08/29)
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- Structurally Simple Benzylidene-Type Photolabile Diol Protecting Groups
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Two structurally simple photolabile protecting groups for releasing 1,2- and 1,3-diols have been developed. The diols can be protected in high yields and released from their corresponding acetals with high chemical efficiency.
- Ding, Xiong,Devalankar, Dattatray A.,Wang, Pengfei
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p. 5396 - 5399
(2016/11/06)
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- 3-hydroxyl oxygen heterocyclic butane preparation method of compound
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The invention discloses a synthetic method of a 3-hydroxy oxetane compound shown as a formula I. The method provided by the invention employs substituted glycerol I-1 as a raw material, which is subjected to condensation with aldehydes and ketones compounds to obtain a compound I-2; the I-2 is subjected to R2 protection to obtain a compound I-3; the compound I-3 is subjected to removal of aldehydes and ketones protecting groups to obtain a compound I-4; the compound I-4 is subjected to intramolecular cyclization to obtain a compound I-5; and the compound I-5 is subjected to removal of R2 protection to obtain a target compound I. Although the method has a long route, the reaction conditions are mild, and the post treatment and detection are convenient; therefore, the method is suitable for industrialized production.
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Paragraph 0032; 0037; 0039
(2016/10/07)
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- Synthesis of Monoalkyl Glyceryl Ethers by Ring Opening of Glycidol with Alcohols in the Presence of Lewis Acids
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The present work deals with the production of monoalkyl glyceryl ethers (MAGEs) through a new reaction pathway based on the reaction of glycidol and alcohols catalyzed by Lewis acid-based catalysts. Glycidol is quantitatively converted with high selectivity (99 %) into MAGEs under very mild reaction conditions (80 °C and 0.01 mol % catalyst loading) in only 1 h using Al(OTf)3 or Bi(OTf)3 as catalyst. The proposed method enhances the choice of possible green synthetic approaches for the production of value-added products such as MAGEs.
- Cucciniello, Raffaele,Ricciardi, Maria,Vitiello, Rosa,Di Serio, Martino,Proto, Antonio,Capacchione, Carmine
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p. 3272 - 3275
(2016/12/16)
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- Glycerol etherification with benzyl alcohol over sulfated zirconia catalysts
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Glycerol (GLY) etherification with benzyl alcohol (BA) was conducted with different zirconia-based heterogeneous acid catalysts, aiming to produce mono- (ME) and dibenzyl glycerol ethers (DE). Physicochemical properties of the prepared catalysts were obtained through XRD, SEM and adsorption of ammonia. The catalytic tests were performed at different temperatures (120-140°C) and initial reactant mass ratios (GLY:BA 1:1 and 2:1). The highest BA conversions were obtained with the catalyst having the highest sulfuric acid content (2S/ZrO2). An increase in the reaction temperature and the GLY:BA initial mass ratio led to an increase in the BA conversion. Two kinetic models (a potential and a hyperbolic approach) were proposed to describe the process performance, including not only reactants evolution with time, but also that of ME, DE and the undesired self-condensation product of BA (benzyl ether, BE). Kinetic parameters for each model were estimated by data fitting and both models were able to accurately describe the evolution of the system, in terms of reactants and product distribution as a function of time under the experimental conditions studied.
- Jaworski, María A.,Rodríguez Vega, Sergio,Siri, Guillermo J.,Casella, Mónica L.,Romero Salvador, Arturo,Santos López, Aurora
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- HIV PROTEASE INHIBITORS AND METHODS FOR USING
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Compounds that inhibit proteolytic enzymes of Human Immunodeficiency Virus (HIV) are described. Preparation of the inhibitors, pharmaceutical compositions containing them, and uses of the compounds or compositions for the treatment of HIV infections are also described.
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Page/Page column 26-27
(2011/06/10)
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- Synthesis and elucidation of absolute stereochemistry of salaprinol, another thiosugar sulfonium sulfate from the ayurvedic traditional medicine Salacia prinoides
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Synthesis and elucidation of absolute stereochemistry of salaprinol (3) isolated from the root and stems of Salacia prinoides, which has been used for the treatment of diabetes in India, Sri Lanka, and Southeast Asia countries, is described. Compound 3 an
- Tanabe, Genzoh,Sakano, Mika,Minematsu, Toshie,Matusda, Hisashi,Yoshikawa, Masayuki,Muraoka, Osamu
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p. 10080 - 10086
(2008/12/22)
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- ANTIOXIDANT POLYMERS CONTAINING [1,2]-DITHIOLANE MOIETIES AND USES THEREOF
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The present invention describes polymers containing 1,2-dithiolanes capable of acting as scavengers of free radicals, metals and reactive oxygen species. Also described are methods of synthesizing the antioxidant 1,2-dithiolane derivatives and polymerization thereof to produce biodegradable antioxidant polymers. The antioxidant polymers of the present invention may be used to treat diseases or conditions caused by oxidative stress and other free radical mediated conditions. The antioxidant polymers may also be used for the preparation of antioxidant particulate delivery devices of therapeutic agents.
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Page/Page column 57-58
(2008/12/07)
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- Flexible cyclic ethers/polyethers as novel P2-ligands for HIV-1 protease inhibitors: Design, synthesis, biological evaluation, and protein-ligand X-ray studies
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We report the design, synthesis, and biological evaluation of a series of novel HIV-1 protease inhibitors. The inhibitors incorporate stereochemically defined flexible cyclic ethers/polyethers as high affinity P2-ligands. Inhibitors containing small ring 1,3-dioxacycloalkanes have shown potent enzyme inhibitory and antiviral activity. Inhibitors 3d and 3h are the most active inhibitors. Inhibitor 3d maintains excellent potency against a variety of multi-PI-resistant clinical strains. Our structure-activity studies indicate that the ring size, stereochemistry, and position of oxygens are important for the observed activity. Optically active synthesis of 1,3-dioxepan-5-ol along with the syntheses of various cyclic ether and polyether ligands have been described. A protein-ligand X-ray crystal structure of 3d-bound HIV-1 protease was determined. The structure revealed that the P2-ligand makes extensive interactions including hydrogen bonding with the protease backbone in the S2-site. In addition, the P2-ligand in 3d forms a unique water-mediated interaction with the NH of Gly-48.
- Ghosh, Aran K.,Gemma, Sandra,Baldridge, Abigail,Wang, Yuan-Fang,Kovalevsky, Andrey Yu.,Koh, Yashiro,Weber, Irene T.,Mitsuya, Hiroaki
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experimental part
p. 6021 - 6033
(2009/10/23)
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- Benzimidazole compound
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An object of the present invention is to provide a novel chemical compound useful as a therapeutic or prophylactic agent for acid-related diseases, having an excellent inhibitory effect against gastric acid secretion, an excellent effect of maintaining the inhibitory effect against gastric acid secretion, thereby maintaining intragastric pH high for a long time, and having more safety and appropriate physicochemical stability. Provided is a compound represented by where R1 and R3 may be the same or different and each represent a hydrogen atom or a C1-C6 alkyl group; R2 represents (5,5-dimethyl-1,3-dioxan-2-yl)methoxy group, 5,7-dioxaspiro[2.5]oct-6-ylmethoxy group, 1,5,9-trioxaspiro[5.5]undec-3-ylmethoxy group, or (2,2-dimethyl-1,3-dioxan-5-yl)methoxy group; R4, R5, R6 and R7 represent a hydrogen atom, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group or C1-C6 haloalkoxy group; and W1 represents a single bond, methylene or ethylene group, a salt thereof or a solvate of these.
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Page/Page column 34
(2008/06/13)
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- Simultaneous interaction with base and phosphate moieties modulates the phosphodiester cleavage of dinucleoside 3′,5′-monophosphates by dinuclear Zn2+complexes of Di(azacrown) ligands
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Five dinucleating ligands (1-5) and one trinucleating ligand (6) incorporating 1,5,9-triazacyclododecan-3-yloxy groups attached to an aromatic scaffold have been synthesized. The ability of the Zn2+ complexes of these ligands to promote the transesterification of dinucleoside 3′,5′-monophosphates to a 2′,3′-cyclic phosphate derived from the 3′-linked nucleoside by release of the 5′-linked nucleoside has been studied over a narrow pH range, from pH 5.8 to 7.2, at 90 °C. The dinuclear complexes show marked base moiety selectivity. Among the four dinucleotide 3′,5′-phosphates studied, viz. adenylyl-3′,5′-adenosine (ApA), adenylyl-3′,5′-uridine (ApU), uridylyl-3′,5′-adenosine (UpA), and uridylyl-3′, 5′-uridine (UpU), the dimers containing one uracil base (ApU and UpA) are cleaved up to 2 orders of magnitude more readily than those containing either two uracil bases (UpU) or two adenine bases (ApA). The trinuclear complex (6), however, cleaves UpU as readily as ApU and UpA, while the cleavage of ApA remains slow. UV spectrophotometric and 1H NMR spectroscopic studies with one of the dinucleating ligands (3) verify binding to the bases of UpU and ApU at less than millimolar concentrations, while no interaction with the base moieties of ApA is observed. With ApU and UpA, one of the Zn2+- azacrown moieties in all likelihood anchors the cleaving agent to the uracil base of the substrate, while the other azacrown moiety serves as a catalyst for the phosphodiester transesterification. With UpU, two azacrown moieties are engaged in the base moiety binding. The catalytic activity is, hence, lost, but it can be restored by addition of a third azacrown group on the cleaving agent.
- Wang, Qi,Loennberg, Harri
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p. 10716 - 10728
(2007/10/03)
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- Bifunctional acyclic nucleoside phosphonates. 1. Symmetrical 1,3-bis[(phosphonomethoxy)propan-2-yl] derivatives of purines and pyrimidines
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We report here a general method for the synthesis of new symmetrical bis-phosphonates of acyclic nucleosides. 1,3-Bis[(diisopropoxyphosphoryl) methoxy] derivatives of purine and pyrimidine bases were prepared by their reaction with 1,3-bis[(diisopropoxyphosphoryl)-methoxy]propan-2-yl tosylate. Cytosine, uracil and thymine provided regiospecifically N1-isomers. This alkylation regiospecificity applies to several other tosylates of primary and secondary alcohols as well. 6-Chloropurine and 2-amino-6-chloropurine were alkylated in N9 position. Resulting bis-phosphonates were converted to the respective free phosphonic acids and tested for antiviral and cytostatic activity. Despite the fact that no biological activity was found so far, the outcome of this work can serve as a useful tool in synthesis of novel groups of acyclic nucleoside phosphonates (ANPs).
- Vrbovska, Silvie,Holy, Antonin,Pohl, Radek,Masojidkova, Milena
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p. 543 - 566
(2007/10/03)
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- Enantiodivergent Preparation of Optically Active Oxindoles Having a Stereogenic Quaternary Carbon Center at the C3 Position via the Lipase-Catalyzed Desymmetrization Protocol: Effective Use of 2-Furoates for Either Enzymatic Esterification or Hydrolysis
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Both enantiomers of oxindoles 2a-h, having a stereogenic quaternary carbon center at the C3 position and a different N-protective group, were readily prepared by the lipase-catalyzed desymmetrization protocol. Thus, the transesterification of the prochiral diols 3a-h with 1-ethoxyvinyl 2-furoate 5 was catalyzed by Candida rugosa lipase to give (R)-(+)-2a-h (68-99% ee), in which the use of a mixed solvent, {%N}i{%N}Pr2O (diisopropyl ether)-THF, was crucial. The same lipase also effected the enantioselective hydrolysis of the difuroates 4a-h in a mixture of {%N}i{%N}Pr2O, THF, and H2O to provide the enantiomers (S)-(-)-2a-h (82-99% ee). The products 2 obtained by both methods were stable against racemization. These enzymatic desymmetrization reactions were also applicable for other typical symmetrical difuroates 12b and 15b to provide the racemization-resistant products 13b and 16b.
- Akai, Shuji,Tsujino, Toshiaki,Akiyama, Emi,Tanimoto, Kouichi,Naka, Tadaatsu,Kita, Yasuyuki
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p. 2478 - 2486
(2007/10/03)
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- Original synthesis of linear, branched and cyclic oligoglycerol standards
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A variety of authentic standards of linear, branched and cyclic oligomers of glycerol, with well-defined structures and degrees of polymerisation from 2 to 5, have been efficiently synthesised. Linear oligomers were obtained by means of a convergent approach based on regioselective opening of bis(epoxides) with solketal; branched compounds were synthesised using oxidative cleavage of the corresponding anhydrohexitols as the key step. A 6-exo-trig halocyclisation reaction involving heteroatom-tethered unsaturated alcohols permitted an efficient synthesis of the precursors of selected cyclic dimers; larger cyclic oligomers were prepared by two one-pot Williamson reactions using a ditriflate derived from diglycerol. All these methodologies permitted further scaling up.
- Cassel, Stephanie,Debaig, Catherine,Benvegnu, Thierry,Chaimbault, Patrick,Lafosse, Michel,Plusquellec, Daniel,Rollin, Patrick
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p. 875 - 896
(2007/10/03)
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- Cleavage of MEM ethers by tetrahalozincate reagents
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A modification of the zinc halide-mediated removal of the MEM group is described. By the expedient of adding two molar equivalents of ethereal hydrogen chloride or of lithium halide, the method is extended to substrates which otherwise chelate the zinc reagent without undergoing deprotection. The compatibility of the resulting reagent Systems with other functional groups is demonstrated, and examples are presented where deprotection of mono-MEM-protected 1,2- and 1,3-diols can be carried out, avoiding the cyclisation which occurs normally.
- Herbert, John M.,Knight, Julian G.,Sexton, Brian
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p. 15257 - 15266
(2007/10/03)
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- Selective monoalkylation of acyclic diols by means of dibutyltin oxide and fluoride salts
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Fluoride anion was found to promote monoalkylation reaction of diols by the stannylene acetal method, and selective monoalkylation of various acyclic diols was accomplished in good yields under mild conditions by employing this new method. Functional groups such as carboxylic acid ester, carboxamide, carbamate, nitrile, alkyl chloride, and ether were not affected under the reaction conditions.
- Nagashima,Ohno
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p. 1972 - 1982
(2007/10/02)
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- Antihypertensive phosphate derivatives
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Antihypertensive phosphate derivatives having the following formula are described: STR1 wherein X is a C1 -C24 branched or straight chain alkyl group; R is selected from the group consisting of hydrogen and C1 -C4 alkyl, with the proviso that at least one R group is not hydrogen; T is selected from the group consisting of hydrogen and STR2 wherein R1 is selected from the group consisting of hydrogen, C1 -C4 branched or straight chain alkyl, C1 -C4 branched or straight chain alkoxy and C1 -C4 branched or straight chain alkylamino; Q is a bivalent radical selected from the group consisting of --(CH2)p -- and --(CHR1)p --, wherein p is an integer from 2 to 12 and the moiety --(CHR1)p -- represents an alkylene chain which is substituted by one or more C1 -C10 alkyl groups or phenyl groups; Z is selected from the group consisting of STR3 wherein R2 may be chain alkyl and q is an integer from 4 to 7; in either the racemic or in the optically active form.
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- SYNTHESIS AND CHARACTERIZATION OF 1-O-α-LACTOSYL-(R,S)-GLYCEROLS AND 1-O-α-LACTOSYL-3-O-β-LACTOSYL-(R,S)-GLYCEROLS
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Coupling of 2,3,6,2',3',4',6'-hepta-O-benzyl-α-lactosyl bromide with an equimolar amount of 1-O-acetyl-2-O-benzyl-(R,S)-glycerols in the presence of tetraethylammonium bromide and 4 Angstroem molecular sieves in 1,2-dichloroethane afforded 3-O-acetyl-2-O-
- Hronowski, Lucian J. J.,Szarek, Walter A.,Hay, George W.,Krebs, Anita,Depew, William T.
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- SYNTHESIS AND CHARACTERIZATION OF 1-O-β-LACTOSYL-(R,S)-GLYCEROLS AND 1,3-DI-OΒ-LACTOSYLGLYCEROL
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The synthesis of 1-O-β-lactosyl-(R,S)-glycerols was achieved by three methods: (a) in 25percent yield by the trimethylsilyl trifluoromethanesulfonate-promoted reaction of octa-O-acetyl-β-lactose (11) with ca. 0.5 mol-equiv. of 2-O-benzylglycerol (4), (b)
- Hronowski, Lucjan J. J.,Szarek, Walter A.,Hay, George W.,Krebs, Anita,Depew, William T.
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p. 203 - 218
(2007/10/02)
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- Lipase-Catalyzed Irreversible Transesterification for Preparative Synthesis of Chiral Glycerol Derivatives
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An irreversible, lipase-catalysed transesterification using enol ester as an acylating agent has been developed for preparative enantioselective acylation of meso-1,3-diols.
- Wang, Yi-Fong,Wong, Chi-Huey
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p. 3127 - 3129
(2007/10/02)
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- STEREOCONTROLLED SYNTHESIS OF A TRANS-ANTI-TRANS TRICYCLE VIA A TRANSANNULAR DIELS-ALDER STRATEGY.
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Transannular Diels-Alder reaction of trans-cis-cis macrocyclic triene 20 yields trans-syn-cis tricycle 21 which is converted into trans-anti-trans tricycle 24 by epimerization at C9 after appropriate functional group transformation.
- Marinier, Anne,Deslongchamps, Pieere
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p. 6215 - 6218
(2007/10/02)
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- Phosphocholine derivatives having antihypertensive action
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Phosphocholine derivatives and compositions are described which are useful as hypotensive agents and in the treatment of hypertension in warm-blooded animals.
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- Enzymatic Differentiation of the Enantiotopic Hydroxymethyl Groups of Glycerol; Synthesis of Chiral Building Blocks
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The prochiral (3b), derived from glycerol, was transformed by enantioselective, enzymatic hydrolysis into the central chiral building block (R)-(4) of high enantiometric purity, which was further elaborated into a variety of chiral building blocks with th
- Breitgoff, Detlev,Laumen, Kurt,Schneider, Manfred P.
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p. 1523 - 1524
(2007/10/02)
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- NEW POTENTIAL IMMUNOENHANCING COMPOUNDS. II. SYNTHESES OF 1-DEOXY-1-THIOPHOSPHATIDYLCHOLINE DERIVATIVES
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The syntheses of four 1-deoxy-1-thiophosphatidylcholine derivatives are described.
- Nali, Micaela,Rindone, Bruno,Bosone, Enrico,Farina, Paolo,Innocenti, Sergio,Valcavi, Umberto
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- Facile synthesis of platelet-activating factor and racemic analogues containing unsaturation in the sn-1-alkyl chain
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Platelet-activating factor, (PAF, 1-O-hexadecyl-2-acetyl-sn-glycero-3-phophocholine), and octadecyl-PAF were synthesized chemically as the racemates. The sn-1-O-alkyl isomers were isolated after treatment of the racemates with phospholipase A2 and subsequent reacetylation of the 1-O-alkyl-2-lyso-sn-glycero-3-phosphocholines released. Analogues of PAF containing unsaturated alkyl moieties at the sn-1 position were synthesized by utilizing the methoxyethoxymethyl protecting group as a novel method for preparing unsaturated alkyl lipids. This procedure provides a facile means for preparing unsaturated ether phospholipids of defined structure that may be tritiated to high radiospecific activity for metabolic studies. Unsaturation in the alkyl chain had minimal effect on the bioactivities examined in this study.
- Surles,Wykle,O'Flaherty,Salzer,Thomas,Snyder,Piantadosi
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- 5-Benzyloxy-1,3-dioxanes
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Herbicidal compositions containing compounds of the formula STR1 where R2 is hydrogen, hydrocarbyl or substituted hydrocarbyl radical; R2a is hydrogen or methyl and R2 and R2a may together form a ring; R5 is hydrogen, alkyl, haloalkyl or cyanoalkyl; Rr is aryl, substituted aryl or heterocyclyl.
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- Synthesis of glycerol 1,3-dihexadecyl ether.
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The synthesis of 1,3-dihexadecyloxy-2-propanol (glycerol 1,3-dihexadecyl ether) is reported. The method is applicable to the preparation of other 1,3-disubstituted glycerols where the substituents are not affected by acid or by catalytic hydrogenolysis conditions.
- Damico,Callahan,Mattson
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