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Usage

Uses

Used in Pharmaceutical Industry:
2,3,4-Tri-O-acetyl-beta-L-arabinopyranosyl 2,2,2-TrichloroacetiMidate is utilized as a component in drug delivery systems for its ability to target specific cells or tissues, thereby enhancing the efficacy and selectivity of therapeutic agents. This targeted approach minimizes side effects and improves treatment outcomes for various diseases.
Used in Biomedical Research:
In the realm of biomedical research, 2,3,4-Tri-O-acetyl-beta-L-arabinopyranosyl 2,2,2-TrichloroacetiMidate serves as a valuable tool for studying the interactions between biological molecules and cellular structures. Its unique properties allow researchers to gain insights into fundamental biological processes, which can inform the design of new drugs and therapies.
Used in Imaging Techniques:
2,3,4-Tri-O-acetyl-beta-L-arabinopyranosyl 2,2,2-TrichloroacetiMidate is also employed in imaging techniques to visualize and monitor biological processes in real-time. Its capacity to bind to specific cellular targets enables the development of imaging agents that can provide detailed information about the location and activity of these targets within living organisms.
Overall, 2,3,4-Tri-O-acetyl-beta-L-arabinopyranosyl 2,2,2-TrichloroacetiMidate's multifaceted applications across different industries underscore its significance in advancing our understanding of biological systems and in the development of more effective medical treatments.

InChI:InChI=1/C13H16Cl3NO8/c1-5(18)22-8-4-21-11(25-12(17)13(14,15)16)10(24-7(3)20)9(8)23-6(2)19/h8-11,17H,4H2,1-3H3/t8-,9+,10+,11+/m0/s1

Upstream product

• 106820-14-8 2,3,4-Tri-O-acetyl-D-xylopyranose 
• 545-06-2 trichloroacetonitrile 
• 62446-93-9 1,2,3,4-tetra-O-acetyl-D-xylopyranose 
• 1233-03-0 α-D-xylopyranose tetraacetate 
• 7296-56-2 β-L-arabinopyranose 
• 4258-00-8 1,2,3,4-tetra-O-acetyl-β-L-arabinopyranose 
• 107961-32-0 Acetic acid (1R,2R)-2-acetoxy-1-((S)-1-acetoxy-2-oxo-ethyl)-3-hydroxy-propyl ester 
• 100924-40-1 2,3,4-tri-O-acetyl-L-arabinose 
• 10369-25-2 2,3,4-tri-O-acetyl-D-arabinopyranose 
• 10369-25-2 (3R,4R,5R)-2-hydroxytetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 4627-30-9 (3R,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 
• 108646-05-5 (3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 
• 28697-53-2 D-arabinopyranose 
• 5139-19-5 2,3,4,5-tetra-O-acetyl-L-arabinose 

Downstream Products

• 72661-85-9 benzyl 2,3,2',3',4'-penta-O-acetyl-β-xylobioside 
• 162088-97-3 2''-iodobenzyl 2,3,2',3',4'-penta-O-acetyl-1-thio-β-xylobioside 
• 162088-92-8 2-nitrophenyl O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-(1<*>4)-2,3-di-O-acetyl-β-D-xylopyranoside 
• 162088-89-3 4-nitrophenyl tri-O-acetyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-acetyl-β-D-xyloside 
• 66912-32-1 4-Methylumbelliferyl-β-D-ribopyranosid 
• 38088-60-7 methyl 3,4-O-isopropylidene-β-L-arabinopyranoside 
• 5328-63-2 methyl-β-D-arabinopyranoside 
• 475101-58-7 4-methoxyphenyl 2,3-O-isopropylidene β-D-xylopyranoside 
• 13299-09-7 p-Methoxyphenyl β-D-xylopyranoside 

Relevant academic research and scientific papers

Preparation of Tea Aroma Precursor Glycosides: An Efficient and Sustainable Approach via Chemical Glycosidation

Tea aroma precursor glycosides are plant-derived natural products with great economic value. However, the preparation of these glycosides remains largely overlooked in the past decades. Herein, we report a mild, efficient, and sustainable chemocatalytic procedure for the production of tea aroma precursor glycosides. During the study of the glycosidation, the catalysts were found to be decisive in the product formation favoring different reaction pathways; in addition, the influence of molecular sieves was elucidated. With regard to these findings, the serious problem of the competing orthoester formation side reaction was successfully overcome with low catalyst loading (1 mol %) and the use of 5 ? molecular sieves, leading to the preparation of a variety of tea aroma precursor β-d-glucopyranosides and β-primeverosides on a gram scale in high yields in an economical way. Taken together, the current approach features catalytic glycosidation with non-toxic and low-cost catalysts, demonstrates highly favorable greenness and sustainability, and promises industrial production of tea aroma precursor glycosides.

Total Synthesis of (+)-Erogorgiaene and the Pseudopterosin A?F Aglycone via Enantioselective Cobalt-Catalyzed Hydrovinylation

Due to their pronounced bioactivity and limited availability from natural resources, metabolites of the soft coral Pseudopterogorgia elisabethae, such as erogorgiaene and the pseudopterosines, represent important target molecules for chemical synthesis. We have now developed a particularly short and efficient route towards these marine diterpenes exploiting an operationally convenient enantioselective cobalt-catalyzed hydrovinylation as the chirogenic step. Other noteworthy C?C bond forming transformations include diastereoselective Lewis acid-mediated cyclizations, a Suzuki coupling and a carbonyl ene reaction. Starting from 4-methyl-styrene the anti-tubercular agent (+)-erogorgiaene (>98 % ee) was prepared in only 7 steps with 46 % overall yield. In addition, the synthesis of the pseudopterosin A aglycone was achieved in 12 steps with 30 % overall yield and, surprisingly, was found to exhibit a similar anti-inflammatory activity (inhibition of LPS-induced NF-κB activation) as a natural mixture of pseudopterosins A?D or iso-pseudopterosin A, prepared by β-D-xylosylation of the synthetic aglycone.

Tea leaf perfumery precursor glucoside and synthesizing method thereof

The invention relates to a tea leaf perfumery precursor glucoside and a synthesizing method thereof. The synthesizing method comprises the following steps of synthesizing ten glucosides including aromatic alcohol ( alkanol )-beta -D-glucosides and aromatic alcohol (alkanol )-beta -D-primrose indicans. The synthesizing method disclosed by the invention is a glucoside synthesizing method which is good in selectivity, high in production rate and low in cost.

Synthetic method of rhodiola rosea active ingredient rosavin or rosarin

The present invention provides a synthetic method of rhodiola rosea active ingredient rosavin or rosarin. A convergent synthetic strategy is adopted, rosin is used as a starting material and modifiedinto sugar acceptors through protection and deprotection strategies, then sugar acceptors and sugar donors formed by arabinopyranose and arabinyl furanose in presence of an accelerator quickly and efficiently conduct synthesis of rosavin and rosarin. The related synthetic method is cheap and easy-to-obtain in raw materials and mild in reaction conditions, the obtained product is high in purity, and compared with currently reported linear synthesis strategy, the method has very good industrialization prospects.

Monosaccharide Analogues of Anticancer Peptide R-Lycosin-I: Role of Monosaccharide Conjugation in Complexation and the Potential of Lung Cancer Targeting and Therapy

Glycoconjugation is a promising modification strategy for the optimization of peptide drugs. In this study, five different monosaccharide derivatives (7a-e) were covalently linked to the N-terminal of R-lycosin-I, which yielded five glycopeptides (8a-e). They demonstrated increased or reduced cytotoxicity depending on monosaccharide types, which might be explained by the changes of physicochemical properties. Among all synthesized glycopeptides, only 8a exhibited increased cytotoxicity (IC50 = 9.6 ± 0.3 μM) and selectivity (IC50 = 37.4 ± 5.9 μM). The glucose transporter 1 (GLUT1) with high expression in cancer cells was approved to be involved in the cytotoxicity and selectivity enhancement of 8a. Furthermore, 8a but not R-lycosin-I inhibited tumor growth in the nude mice xenograft model without generating side effects intraperitoneally. Taken together, this study reveals the different monosaccharide roles in peptide modification and also provides an optimized anticancer peptide with high activity and selectivity, that is, 8a might be a promising lead for developing anticancer drugs.

Synthesis and Properties of Alkoxyethyl β-d-Xylopyranoside

In order to improve the water solubility of sugar-based surfactants, alkyl β-d-xylopyranosides, novel sugar-based surfactants, 1,2-trans alkoxyethyl β-d-xylopyranosides, with alkyl chain length n = 6–12 were stereoselectively prepared by the trichloroacetimidate method. Their properties including hydrophilic–lipophilic balance (HLB) number, water solubility, surface tension, emulsification, foamability, thermotropic liquid crystal, and hygroscopicity were investigated. The results indicated that their HLB number decreased with increase of alkyl chain, the water solubility improved since the hydrophilic oxyethene (─OCH2CH2─) fragment was introduced. The dissolution process was entropy driven at 25–45 °C for alkyl chain length n = 6–10. Octyloxyethyl β-d-xylopyranoside had the best foaming ability. Nonyloxyethyl β-d-xylopyranoside had the best foam stability and the emulsifying ability was better in toluene/water system than in rapeseed oil/water system. The surface tension of in aqueous solution dropped to 27.8 mN m?1 at the critical micelle concentration, and it also showed the most distinct thermotropic liquid phases with cross pattern texture upon heating and the fan schlieren texture on cooling. Hexyloxyethyl β-d-xylopyranoside possessed the strongest hygroscopicity. Based on the effective improvement of water solubility, the prepared alkoxyethyl β-d-xylopyranosides showed excellent surface activity and are expected to develop their practical application as a class of novel sugar-based surfactants.

Total Synthesis of Pseudomonas aeruginosa 1244 Pilin Glycan via de Novo Synthesis of Pseudaminic Acid

Pseudaminic acid (Pse) is a nonulosonic acid unique to bacterial species, found as a component of important cell surface glycans and glycoproteins in various pathogenic species, such as the critical hospital threat Pseudomonas aeruginosa. Herein we present the development of a facile and scalable de novo synthesis of Pse and its functionalized derivatives from easily available Cbz-l-allo-threonine methyl ester (16 steps in 11% yield). The key reactions in our de novo synthesis involve the diastereoselective glycine thioester isonitrile-based aldol-type reaction to create the 1,3-anti-diamino skeleton, followed by the Fukuyama reduction and the indium-mediated Barbier-type allylation. Moreover, we have studied the glycosylation of the Pse glycosyl donors and identified the structural determinants for its glycosylation diastereoselectivity, which enabled us to complete the total synthesis of P. aeruginosa 1244 pilin trisaccharide α-5NβOHC47NFmPse-(2→4)-β-Xyl-(1→3)-FucNAc.

A kind of mountain Lotus leaf derivative and its preparation and use

The invention provides a kind of diphyllin derivatives, and a preparation method and application thereof. The related diphyllin derivatives have the chemical structural general formula shown as formula A in the specification. The invention discloses the structural general formula of the above compounds, a synthetic method, application as a bactericide, a plant virus resistant agent and a plant activating agent, and a processing technology of mixing the above compounds with an agriculturally-acceptable assistant or synergist for preparing the bactericide, the plant virus resistant agent and the plant activating agent. The invention also discloses application of combinations of the compounds and commercial bactericides, plant virus resistant agents and plant activating agents to control agricultural, forestry and garden diseases, insect attack, mite attack, virus attack and the like, and a preparation method. The invention also discloses application of the above compounds to prepare medicines and auxiliary medicines for treating cancers and immune imbalance, and application of the combinations of the above compounds.

Novel xylosidesurfactant

The invention belongs to the technical field of surfactants for fine chemistry and discloses a novel sugar-based surfactant, namely, alkoxyethyl-beta-D-xylopyranoside in order to solve the problem of limitation to application of traditional alkyl glycoside as the surfactant due to the fact water solubility of traditional alkyl glycoside is gradually reduced with increase of carbon chain length. Compared with traditional alkyl glycoside with the same carbon chain length, the surfactant has better water solubility and surface activity as well as selectable and controllable foaming capacity and emulsifying property. Besides, raw materials for synthesis comprisexylose obtained from waste crop leftovers and naturally-sourced fatty alcohol and have rich sources. The glycoside can be widely applied to application industries such as biochemical engineering, pharmacy, pesticides, food processing, cosmetics, scientific research and the like.

Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors

A series of 7-substituted coumarins incorporating various glycosyl moieties were synthesized and investigated for the inhibition of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). These coumarins were very weak or ineffective as inhibitors of the housekeeping, offtarget isoforms CA I and II, but some of them inhibited tumor-associated CA IX and XII in the low nanomolar range. They also significantly inhibited the growth of primary tumors by the highly aggressive 4T1 syngeneic mouse mammary tumor cells at 30 mg/kg, constituting interesting candidates for the development of conceptually novel anticancer drugs. Because CA IX is overexpressed in hypoxic tumors and exhibits very limited expression in normal tissues, such compounds may be useful for treating cancers not responsive to classic chemo- and radiotherapy.