- Class II histocompatibility complex expression enhancing compound and preparation method and application thereof
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The invention discloses a class II histocompatibility complex (MHC class II) expression enhancing compound and a preparation method and application thereof. Experiments prove that the compound has a remarkable class II histocompatibility complex expression enhancing effect, remarkable effect in enhancing class II histocompatibility complex tumor neoantigen presentation and promoting tumor tissue CD4 + T cell infiltration, and remarkable effect in inhibiting tumor growth when the compound is used independently or combined with existing immunotherapy means drugs.
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Paragraph 0099-0102
(2021/08/28)
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- Greener synthesis of pristane by flow dehydrative hydrogenation of allylic alcohol using a packed-bed reactor charged by pd/c as a single catalyst
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Our previous work established a continuous-flow synthesis of pristane, which is a saturated branched alkane obtained from a Basking Shark. The dehydration of an allylic alcohol that is the key to a tetraene was carried out using a packed-bed reactor charged by an acid–silica catalyst (HO-SAS) and flow hydrogenation using molecular hydrogen via a Pd/C catalyst followed. The present work relies on the additional propensity of Pd/C to serve as an acid catalyst, which allows us to perform a flow synthesis of pristane from the aforementioned key allylic alcohol in the presence of molecular hydrogen using Pd/C as a single catalyst, which is applied to both dehydration and hydrogenation. The present one-column-two-reaction-flow system could eliminate the use of an acid catalyst such as HO-SAS and lead to a significant simplification of the production process.
- Fukuyama, Takahide,Furuta, Akihiro,Hirobe, Yuki,Hyodo, Mamoru,Kasakado, Takayoshi,Ryu, Ilhyong
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- Flow Dehydration and Hydrogenation of Allylic Alcohols: Application to the Waste-Free Synthesis of Pristane
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Hydroxy-substituted sulfonic acid functionalized silica (HO-SAS) in combination with THF containing a small amount of water as a solvent proved to be a reliable system for the dehydration of allylic alcohols. This process generally caused dehydration within 1 min through a column reactor charged with HO-SAS. The flow dehydration was sequenced by flow hydrogenation, which resulted in the synthesis of pristane. A scalable flow synthesis of pristane was successfully performed and afforded 10 g of pristane after an operation of 2 h. We also performed dehydration and hydrogenation by using a mixed column of HO-SAS and 10 % Pd/C.
- Furuta, Akihiro,Hirobe, Yuki,Fukuyama, Takahide,Ryu, Ilhyong,Manabe, Yoshiyuki,Fukase, Koichi
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supporting information
p. 1365 - 1368
(2017/03/23)
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- A method for synthesizing basking shark alkane
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The present invention discloses a novel method for chemically synthesizing pristane with isophytol as a starting material. Isophytol is used, and pristane is prepared through oxidation, a methyl Grignard reaction, sulfonylation, halogenation and reduction. The method in the present invention, as compared with the conventional synthesizing method, adopts cheap raw materials, avoids high pressure hydrogenation reactions, and solves the problems of methyl migration caused by a dehydration reaction or isomerization caused by cyclization in the conventional synthesizing method. The method of the present invention is suitable for industrial production of pristane.
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- A method for synthesizing basking shark alkane
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The invention discloses a novel method for chemically synthesizing pristane on the basis of a starting material isophytol. By the method, pristane is obtained by oxidizing isophytol and performing epoxidation, lewis acid open-loop reaction, sulfonylation, halogenation and reduction. Compared with a conventional synthesis method, the method has the advantages that the raw material is low in cost, high-pressure hydrogenation reaction is avoided, the problem of methyl transfer or cyclization isomerization caused by dehydration reaction in the conventional synthesis method is solved, and the method is suitable for the industrial production of pristane.
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- The formation features of C10–C20 regular petroleum isoprenanes
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To model the formation processes of C10–C20 petroleum isoprenanes, thermolysis of regular and irregular C20–C40 isoprenanes (phytane, crocetane, squalane, and lycopane) and the suggested precursors of regular pe
- Gordadze,Giruts,Poshibaeva,Koshelev
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p. 672 - 676
(2016/10/04)
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- Renaissance of traditional organic reactions under microfluidic conditions: A new paradigm for natural products synthesis
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Continuous flow synthesis for bioactive natural products is described. Efficient procedures using the microfluidic system were developed for the large-scale synthesis of important synthetic units of asparagine-linked oligosaccharide in glycoprotein. Advantageous aspects of microfluidic conditions, i.e., efficient mixing, fast heat transfer, and residence time control led to cation-mediated reactions, such as a-sialylation, β-mannosylation, and reductive opening of the benzylidene acetal groups in high yields. Microfluidic dehydration was developed for the industrial-scale synthesis of the immunostimulating natural terpenoid, pristane. The base-mediated aldol condensation in an aqueous biphasic system enabled the multigram synthesis of β-hydroxyketones in high yields. 2009 American Chemical Society.
- Tanaka, Katsunori,Fukase, Koichi
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experimental part
p. 983 - 990
(2010/04/22)
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- Large-scale synthesis of immunoactivating natural product, pristane, by continuous microfluidic dehydration as the key step
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(Figure Presented) An efficient protocol of dehydration was developed under microfluidic conditions. The method was applied to a multikilogram synthesis of pristane, a biologically important natural product, which is now widely used as an adjuvant for monoclonal antibody production.
- Tanaka, Katsunori,Motomatsu, Shinya,Koyama, Koichi,Tanaka, Shin-Ichi,Fukase, Koichi
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p. 299 - 302
(2007/10/03)
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- Pyrolytic formation of C19 isoprenoid hydrocarbons from dihydrophytol: In relation to the genesis of pristane in petroleum
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This study was concluded to elucidate a pathway for formation of C19 isoprenoid hydrocarbons (isops) in petroleum from chlorophylls. C19 isops are predominantly produced when dihydrophytol is heated at 320°C for a period ranging from 1 to 5 h under vacuum while C20 isops are predominantly produced when chlorophyll a or phytol is heated. A radical chain reaction of decomposition of dihydrophytol is proposed as plausible pathway for producing C19 isops.
- Ishiwatari, Mariko,Yamada, Keita,Ishiwatari, Ryoshi
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p. 206 - 207
(2007/10/03)
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