- Ferric Salt Catalyzed Oxygenation of Cycloalkanones to Oxo Esters by Molecular Oxygen
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Ferric salts catalyzed the regiospecific oxygenation of cycloalkanones by molecular oxygen to give oxo esters in the presence of aliphatic alcohol under mild conditions.
- Ito, Satoru,Matsumoto, Masakatsu
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- IONIZABLE AMINE LIPIDS AND LIPID NANOPARTICLES
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The disclosure provides ionizable amine lipids and salts thereof (e.g., pharmaceutically acceptable salts thereof) useful for the delivery of biologically active agents, for example delivering biologically active agents to cells to prepare engineered cells. The ionizable amine lipids disclosed herein are useful as ionizable lipids in the formulation of lipid nanoparticle-based compositions.
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Page/Page column 126; 127
(2020/11/04)
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- LIPIDS AND LIPID COMPOSITIONS FOR THE DELIVERY OF ACTIVE AGENTS
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This invention provides for a compound of formula (I): or a pharmaceutically acceptable salt thereof, wherein R1-R4, n and p are defined herein. The compounds of formula (I) and pharmaceutically acceptable salts thereof are cationic lipids useful in the delivery of biologically active agents to cells and tissues.
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Page/Page column 98
(2015/07/07)
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- LIPIDS AND LIPID COMPOSITIONS FOR THE DELIVERY OF ACTIVE AGENTS
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This invention provides for a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein R1-R3, n, p, L1 and L2 are defined herein. The compounds of formula (I) and pharmaceutically acceptable salts thereof are cationic lipids useful in the delivery of biologically active agents to cells and tissues.
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Page/Page column 109
(2015/07/07)
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- Introducing an in situ capping strategy in systems biocatalysis to access 6-aminohexanoic acid
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The combination of two cofactor self-sufficient biocatalytic cascade modules allowed the successful transformation of cyclohexanol into the nylon-6 monomer 6-aminohexanoic acid at the expense of only oxygen and ammonia. A hitherto unprecedented carboxylic acid capping strategy was introduced to minimize the formation of the deadend intermediate 6-hydroxyhexanoic acid. For this purpose, the precursor ε-caprolactone was converted in aqueous medium in the presence of methanol into the corresponding methyl ester instead of the acid. Hence, it was shown for the first time that esterases-specifically horse liver esterase-can perform the selective ring-opening of ε-caprolactone with a clear preference for methanol over water as the nucleophile.
- Sattler, Johann H.,Fuchs, Michael,Mutti, Francesco G.,Grischek, Barbara,Engel, Philip,Pfeffer, Jan,Woodley, John M.,Kroutil, Wolfgang
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supporting information
p. 14153 - 14157
(2015/02/19)
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- Designer discodermolide segments via ozonolysis of vinyl phosphonates
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(Chemical Equation Presented) To apply our collection of enantiopure 7-ring vinyl sulfones to probe the anticancer SAR of a series of computer-designed (+)-discodermolide analogs, the ozonolytic reactivity of transposed cyclic vinyl phosphonates was explo
- Du Jourdin, Xavier Mollat,Noshi, Mohammad,Fuchs
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supporting information; experimental part
p. 543 - 546
(2009/07/18)
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- Efficient and selective catalytic oxidative cleavage of α-hydroxy ketones using vanadium-based HPA and dioxygen
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The combination of H3 + n[PMo12 - nVnO 40]·aq (HPA-n, n = 3) and dioxygen provides a clean and regioselective reagent for the homolytic cleavage of various representative α-hydroxy ketones (primary to tertiary) and turns out to be as efficient for the catalytic ring opening of chiral natural products.
- El Aakel,Launay,Atlamsani,Bregeault
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p. 2218 - 2219
(2007/10/03)
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- Photo-cleavage of carbon-carbon bond of α-iodocycloalkanones giving ω,ω-dialkoxyalkanoic ester in alcohol
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The irradiation at λ > 300 nm of α-iodocycloalkanones with a high- pressure mercury lamp in alcohols containing a small amount of water afforded the corresponding ω,ω-dialkoxyalkanoic ester (65-88%) by photochemical cleavage of the C(I)-C=O bond at room temperature. In the case of a commercial fluorescent lamp as the irradiating light source, photochemical ring-opening products were also obtained. The irradiation of 2α-iodo-5α- and 4β-iodo-5β-cholestan-3-ones in methanol gave methyl 2,2-dimethoxy-2,3- seco-5α-cholestan-3-oate and methyl 4,4-dimethoxy-3,4-seco-5β-cholestan-3- oate in 78 and 62% yields, respectively. The photochemical behavior of the cleavage reaction of α-iodocycloalkanones is also discussed on the basis of 2-hydroxycycloalkanone as an intermediate.
- Ji, Shun-Jun,Horiuchi, C. Akira
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p. 1645 - 1652
(2007/10/03)
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- Electrochemical transformations of monooxa- and dioxabicycloalkenes and -bicycloalkanes
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Electrolysis of 2-oxa-and 2,5-dioxabicyclo[n.4.0]alk-1(6)-enes (n = 4, 10) under conditions of direct undivided anodic oxidation in methanol results in their electrochemical mono-and dimethoxylation; electrolysis of the corresponding 2-oxa-and 2,5-dioxabicycloalkanes involves electrochemical cleavage of the bridging carbon - carbon bonds followed by electrooxidative transformation into methyl ω-(2-methoxytetrahydrofuryl)-, ω-(dimethoxymethyl)-, and ω-(1,3-dioxolan-2-yl)alkanoates.
- Ogibin,Terent'ev,Ilovaisky,Nikishin
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p. 2091 - 2099
(2007/10/03)
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- Synthesis of glycoconjugate vaccines against Shigella dysenteriae type 1
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Syntheses of hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglycon-linked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.
- Pozsgay, Vince
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p. 5983 - 5999
(2007/10/03)
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- Electro-organic Chemistry. Part 93. Electro-organic Transformation of Aldehydes and Ketones to α-Hydroxylated Acetals Utilizing Mediators and Some Synthetic Uses of the Products
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Electro-oxidation of aldehydes (R1R2CHCHO) and ketones (R1R2CHCOR3) in methanol containing iodide ion (I-) and KOH gave the corresponding α-hydroxylated acetals in good yields.The first step of this oxidation is explained in terms of the attack of an anodically generated active iodine species 'I+' on enols of R1R2CHCHO and R1R2CHCOR3. α-Hydroxy acetals were useful starting materials as exemplified by reaction with aniline or methyl carbamates in the presence of Lewis acids to afford β-keto amine derivatives.The anodic oxidation of α-hydroxy acetals was also carried out.
- Shono, Tatsuya,Matsumura, Yoshihiro,Inoue, Kenji,Iwasaki, Fumiaki
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- The Preparation of Dioxaprostacyclin Analogues from D-(-)-Ribose
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Using D-(-)-ribose as chiral starting material, we have prepared 1-deoxy-D-ribofuranose by a novel route, and then employed both compounds as precursors of the dioxaprostacyclin analogues (2).
- Heath, Peter,Mann, John,Walsh, E. Brian,Wadsworth, Alan H.
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p. 2675 - 2679
(2007/10/02)
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- Ozonolysis of Symmetrically 1,2-Disubstituted Ethylenes in HCl/Methanol Solutions: Acid Catalyzed Reactions of Primary Cleavage Products
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The ozonolysis of olefins in 1 M anhydrous solutions of hydrogen chloride in methanol at /= 0 deg C was investigated.Upon warm-up of the ozonolysis products, the peroxidic primary fragmentation products were converted into non peroxidic end-products by HCl-catalyzed reactions.Cyclopentene (1a) and cyclohexene (1b), e.g., afforded mixtures of the corresponding α,ω-dialdehydebis(dimethyl acetals) (8), dimethyl α,ω-dicarboxylates (9), and methyl ω-aldehyde dimethyl acetal carboxylates (10).Norbornene (1c) gave a mixture of the correspondingly substituted 1,3-cyclopentane compounds (8c - 10c), phenanthrene (22) gave a mixture of methyl 2'-formyl-2-biphenylcarboxylate (24a), 2,2'-biphenyldicarbaldehyde (24b), and dimethyl 2,2'-biphenyldicarboxylate (24c).A reaction scheme was advanced for the rationalization of the types and the distribution of the products.It was partly substantiated by model reactions.
- Griesbaum, Karl,Neumeister, Joachim
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p. 2697 - 2706
(2007/10/02)
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- NOVEL CARBON-CARBON BOND CLEAVAGE REACTIONS OF α-AZOHYDROPEROXIDES
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1-Phenylazo-1-hydroperoxycyclohexanes, easily prepared by the autoxidation of cyclohexanone phenyl hydrazones, have been found to undergo C(1)-C(2) bond cleavages when treated with acids, bases, or reducing reagents under mild conditions.Thus 6-oxoalkanoic acids and their derivatives have been obtained in good yields from 2-hydroxycyclohexanone derivatives.The 2-hydroxyl group seems to play an important role for the cleavage.
- Utaka, Masanori,Fujita, Yuji,Takeda, Akira
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p. 1607 - 1610
(2007/10/02)
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- OZONOLYTIC CLEAVAGE OF CYCLOALKENES TO TERMINALLY DIFFERENTIATED PRODUCTS
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Conditions are reported which convert cycloalkenes to terminally differentiated product through the intermediacy of α-alkoxy hydroperoxides.
- Schreiber, Stuart L.,Claus, Ronald E.,Reagan, Jeff
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p. 3867 - 3870
(2007/10/02)
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- Process for the preparation of novel unsaturated macrocyclic ketones
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New unsaturated macrocyclic ketones are obtained via a process which consists in reacting a dialdehyde with a tetraalkyldiphosphonate ester. The new ketones are useful intermediates for the preparation of cyclopentadecanone and its higher methyl-homologue, known fragrant substances. New ketones possess also direct utility as musky odorants.
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