69161-59-7Relevant academic research and scientific papers
Diastereoselective Desymmetrization of p-Quinamines through Regioselective Ring Opening of Epoxides and Aziridines
Jadhav, Sandip B.,Chegondi, Rambabu
supporting information, p. 10115 - 10119 (2019/12/24)
A highly diastereoselective desymmetrization of p-quinamines via regioselective ring opening of epoxides and aziridines under mild conditions has been developed. A chairlike six-membered transition state with minimized 1,3-diaxial interactions explains the relative stereoselectivity of the cyclization reaction. This transition-metal free [3 + 3] annulation reaction provides rapid access to fused bicyclic morpholines and piperazines with a tetrasubstituted carbon center in high yields. In addition, it also allows the synthesis of enantioenriched products by using easily accessible chiral nonracemic epoxides and aziridines.
Prepartion method of itraconazole
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Paragraph 0043; 0044; 0045; 0046, (2017/04/29)
The invention discloses a preparation method of itraconazole. Raceme-glycidol which is cheap and easy to obtain is adopted as raw materials, hydroxyls at the two ends are protected by trityl and benzyl and then esterified by 2,4-dichlorobenzene formyl chloride, then, a silylation Grignard addition reaction and a beta-silicyl alcohol elimination reaction are adopted for reducing carbonyl into carbon-carbon double bonds, iodine is adopted for performing an olefin addition reaction and a stereoselectivity ring-closure reaction, triazole replacement and debenzylation are performed, and tosyl is introduced to obtain a compound 9; the compound and a compound 10 are subjected to a condensastion reaction to obtain itraconazole; the overall synthesis process is small in pollution, easy to process, few in by-product, high in reaction selectivity and purity, environmentally friendly, low in production cost and suitable for industrial production; the defects that in the prior art, the selectivity is poor, multiple by-products are produced, the yield is low, and expensive catalysts and reagents with large environmental pollution are avoided are avoided.
Modular synthesis of dihydroxyacetone monoalkyl ethers and isosteric 1-hydroxy-2-alkanones
Güclü, Deniz,Rale, Madhura,Fessner, Wolf-Dieter
supporting information, p. 2960 - 2964 (2015/04/27)
Straightforward methods for the efficient, systematic preparation of libraries of the title compound classes have been evaluated. A general and efficient modular route to dihydroxyacetone monoethers was developed based on trityl glycidol, which, through epoxide opening, oxidation, and deprotection, provided variously alkylated ethers by three routine operations in good overall yields (eight examples, 24-59 %). The preparation of structurally related 1-hydroxyalkanones depends on the availability of the most economic starting materials and on their physicochemical properties. Thus, the most practical one-step approaches consisted of the sec-selective oxidation of short-chain 1,2-diols (≤ C6) using NaOCl, and the direct ketohydroxylation of 1-alkenes (≥ C6) using buffered stoichiometric KMnO4 or catalytic RuO4 with reoxidation by oxone, for which mostly good overall yields were achieved on a multigram scale (nine examples, 15-78 %).
A straightforward approach to substituted 2-(hydroxymethyl)-2,3- dihydrofuro[2,3- b ]pyridines and 3-hydroxy-3,4-dihydro-2 H -pyrano[2,3- b ]pyridines
Hajbi, Youssef,Suzenet, Franck,Khouili, Mostafa,Lazar, Said,Guillaumet, Gerald
experimental part, p. 1349 - 1355 (2010/07/02)
An efficient route to 2-(hydroxymethyl)-2,3-dihydrofuro[2,3-b]pyridines and 3-hydroxy-3,4-dihydro-2H-pyrano[2,3-b]pyridines is reported. The strategy is based on an intramolecular inverse electron demand Diels-Alder reaction starting from 1,2,4-triazines.
Lipase-mediated resolution of 3-hydroxy-4-trityloxybutanenitrile: synthesis of 2-amino alcohols, oxazolidinones and GABOB
Kamal, Ahmed,Khanna, G.B. Ramesh,Krishnaji,Ramu
, p. 1281 - 1289 (2007/10/03)
Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the (S)-alcohol and (R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase (Burkholderia cepacia) immobilized on modified cera
Cyclization strategies for the synthesis of macrocyclic bisindolylmaleimides
Faul,Krumrich
, p. 2024 - 2033 (2007/10/03)
Three new approaches to the synthesis of macrocyclic bisindolylmaleimides 1-4 have been identified. Two strategies afford 8, the penultimate intermediate for the synthesis of 1-4, in 73% and 32% yield by intramolecular cyclization of 31 and 40, respectively. The optimum synthesis of 1 was achieved in nine steps and 15% yield by intramolecular formation of the macrocycle and maleimide in one step by reaction of the sodium indolate of 12 with methyl indole-3-glyoxylate 47. The mechanism of this reaction has been elucidated, using the trityl-protected derivative, to involve initial formation of the tricarbonyl imide 48, followed by irreversible alkylation of the indole nitrogen to generate the 17-membered macrocycle 49. Cyclization of 49 to hydroxymaleimide 50 and subsequent dehydration afforded 8a. This approach eliminated the problem of dimerization observed in the intramolecular cyclization reactions.
Formulations and methods for generating active cytofectin: polynucleotide transfection complexes
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, (2008/06/13)
In the generation of cytofectin:polynucleotide complexes for transfection of cells, formulations, counterions, and reaction conditions for maximizing the transfection include using a cationic amine compound that has the general structure: STR1 wherein Rs
Polyfunctional cationic cytofectins, formulations and methods for generating active cytofectin: polynucleotide transfection complexes
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, (2008/06/13)
Amine containing compounds and their use in the generation of cytofectin:polynucleotide complexes for transfection of cells, formulations, counterions, and reaction conditions for maximizing the transfection include using cationic amine compounds that hav
Insight into Rh(I)-catalyzed cyclization of 6-octen-1-als with a chiral protecting group
Koga,Funakoshi,Matsuda,Sakai
, p. 1857 - 1868 (2007/10/02)
Rh(I)(Wilkinson)[ClRh(PPh3)3]-catalyzed cyclization of 6-octen-als with a chiral protecting group at the C2-position afforded only cis-cyclohexanol derivatives, and in the case of C4-position yielded a mixture of cis and trans cyclohexanol. These findings were remakably different from the case of the C3-position, in which the trans cyclohexanol derivative was obtained. Wilkinson's complex acts as [ClRh(PPh3)3] a Lewis acid, and this bulkier Lewis acid affords higher diastereoselectivity. Rh(I)-catalyzed cyclization of 6-octen-1-al derivatives is not affected by chiral ligands.
