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Penta-O-benzoyl-β-D-glucopyranose is a chemical compound derived from β-D-glucopyranose, a monosaccharide sugar. It is characterized by the presence of five benzoyl groups attached to the hydroxyl groups of the sugar molecule, which significantly alter its properties compared to the parent compound. This derivative is often used in organic synthesis and carbohydrate chemistry, particularly for the preparation of more complex glycosides and other sugar derivatives. The 95% HPLC purity indicates that the product is of high quality, with a minimal amount of impurities, making it suitable for sensitive applications and research purposes.

2592-58-7

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2592-58-7 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 2592-58-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,9 and 2 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 2592-58:
(6*2)+(5*5)+(4*9)+(3*2)+(2*5)+(1*8)=97
97 % 10 = 7
So 2592-58-7 is a valid CAS Registry Number.

2592-58-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name PENTA-O-BENZOYL-Β-D-GLUCOPYRANOSE, 95% HPLC

1.2 Other means of identification

Product number -
Other names Penta-O-benzoyl-D-glucopyranose

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2592-58-7 SDS

2592-58-7Relevant academic research and scientific papers

N-aryl sulfanilamide-N-beta-D-glucopyranose diamide compound and application thereof

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Paragraph 0029-0030, (2021/06/26)

The invention belongs to the technical field of medicines, and relates to a preparation method and medical application of an N1-aryl sulfanilamide-N4-beta-D-glucopyranose diamide compound. The compound is shown in a general formula (I), substituent groups are described in the specification, and the compound shown in the general formula (I) and an optical active body, a diastereoisomer and a pharmaceutically acceptable salt thereof are applied to preparation of anti-tumor drugs. Based on pharmacophore characteristics and subcellular localization of CA IX and XII, a selective CA IX and XII inhibitor is designed and synthesized, polyhydroxy high-polarity glucose is selected as a tail end, a classical pharmacophore aryl sulfanilamide fragment of a targeted CAs active center is introduced through a flexible aliphatic chain and a rigid aromatic structure, the overall structure can selectively inhibit catalytic activity of extracellular CA IX and XII, an anti-tumor effect is achieved, and therefore, the compound has a good application prospect.

Synthesis and inhibition of α-glucosidase of methyl glycyrrhetinate glycosides

Zhang, Wei,Wang, He-Ying,Wang, Huai-Xu,Zhu, Zhen-Yuan

supporting information, p. 1874 - 1880 (2019/07/22)

The synthesis of the methyl glycyrrhetinate glycosides and inhibition of α-glucosidase were studied. The carboxyl group of glycyrrhetinic acid was methylated, and glucose and galactose were introduced into the hydroxyl group to obtain compounds 7 and 12.

Synthesis, molecular docking analysis and biological evaluations of saccharide-modified thiadiazole sulfonamide derivatives

Zhang, Zuo-Peng,Zhong, Ye,Han, Zhen-Bin,Zhou, Lin,Su, Hua-Sheng,Wang, Jian,Liu, Yang,Cheng, Mao-Sheng

, (2021/05/26)

A series of saccharide-modified thiadiazole sulfonamide derivatives has been designed and synthesized by the “tail approach” and evaluated for inhibitory activity against carbonic anhydrases II, IX, and XII. Most of the compounds showed high topological polar surface area (TPSA) values and excellent enzyme inhibitory activity. The impacts of some compounds on the viability of HT-29, MDA-MB-231, and MG-63 human cancer cell lines were examined under both normoxic and hypoxic conditions, and they showed certain inhibitory effects on cell viability. Moreover, it was found that the series of compounds had the ability to raise the pH of the tumor cell microenvironment. All the results proved that saccharide-modified thiadiazole sulfonamides have important research prospects for the development of CA IX inhibitors.

A Substituent-Directed Strategy for the Selective Synthesis of L-Hexoses: An Expeditious Route to L-Idose

See, Nicholas W.,Wimmer, Norbert,Krenske, Elizabeth H.,Ferro, Vito

, p. 1575 - 1584 (2021/03/03)

L-Hexoses are rare but biologically significant components of various important biomolecules. However, most are prohibitively expensive (if commercially available) which limits their study and biotechnological exploitation. New, efficient methods to access L-hexoses and their derivatives are thus of great interest. In a previous study, we showcased a stereoselective Bu3SnH-mediated transformation of a 5-C-bromo-D-glucuronide to an L-iduronide. We have now drawn inspiration from this result to derive a new methodology – one that can be harnessed to access other L-hexoses. DFT calculations demonstrate that a combination of a β-F at the anomeric position and a methoxycarbonyl substituent at C-6 is key to optimising the selectivity for the L-hexose product. Our investigations have also culminated in the development of the shortest known synthetic route to a derivative of L-idose from a commercially available starting material (45 % yield over 3 steps). Collectively, these results address the profound lack of understanding of how to synthesise L-hexoses in a stereoselective fashion.

Delta-oleanolic acid saponin compound and medical application thereof

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Paragraph 0074-0077, (2020/12/31)

The invention discloses a delta-oleanolic acid saponin compound and medical application thereof. The delta-oleanolic acid saponin compound is a compound with a structural formula shown as a formula (I), and pharmaceutically acceptable salt or ester or pro

The synthesis of rare earth metal-doped upconversion nanoparticles coated with d-glucose or 2-deoxy-d-glucose and their evaluation for diagnosis and therapy in cancer

Sharma, K. Shitaljit,Thoh, Maikho,Dubey, Akhil K.,Phadnis, Prasad P.,Sharma, Deepak,Sandur, Santosh K.,Vatsa, Rajesh K.

supporting information, p. 13834 - 13842 (2020/09/07)

Rare earth metal-doped upconversion nanoparticles (UCNPs) are emerging as a new class of biomedical imaging materials due to their higher energy anti-Stokes shift, high optical penetration depth and long term repetitive imaging. In the present study, upconversion nanoparticles based on NaYF4 doped with thulium (Tm) and ytterbium (Yb) were prepared via a thermolysis method using oleic acid as a capping agent and 1-octadecene as a solvent. The X-ray diffraction pattern of the synthesized nanoparticles was found to match the standard hexagonal phase. The nanoparticles were coated with silica using tetraethyl orthosilicate (TEOS) and in order to avoid agglomeration, IGEPAL CO-520 was used as the surfactant. The coatings of SiO2 over NaYF4 were confirmed by the TEM image and XRD pattern. NaYF4@SiO2 was further functionalized by the addition of (3-aminopropyl)trimethoxysilane (APTMS) followed by either d-glucose or 2-deoxy-d-glucose (2-DG). UCNPs-d-glucose and UNCPs-2DG were examined for cell viability (MCF-7 cells) by MTT assay. The cellular uptake of UCNPs in MCF-7 cells was seen in terms of emission of a blue light. Furthermore, the uptake rate of UCNPs coated with 2-deoxy-d-glucose was found to be much faster than that of UCNPs alone under d-glucose starved conditions. The functionalization of UCNPs with 2-deoxy-d-glucose (2-DG) not only increased the uptake of nanoparticles, but also blocked the glycolysis pathway resulting in the inhibition of tumor growth as 2-deoxy-d-glucose (2-DG) is mimicking the d-glucose. The results are indicative that these upconversion nanoparticles may find applications in bio-imaging, removal of tumor by precision surgery, therapy and targeted drug delivery. This journal is

Synthesis of 2-deoxy-d-glucose coated Fe3O4nanoparticles for application in targeted delivery of the Pt(iv) prodrug of cisplatin-a novel approach in chemotherapy

Ballal, Anand,Dubey, Akhil K.,Koijam, Arunkumar S.,Kumar, Chandan,Mukherjee, Sudip,Phadnis, Prasad P.,Sharma, K. Shitaljit,Vatsa, Rajesh K.

supporting information, p. 13863 - 13874 (2020/09/07)

A water soluble Pt(iv) prodrug of cisplatin was synthesized by oxidation of cisplatin followed by treatment with succinic anhydride to achieve easily reducible ester linkage at axial positions which was evidenced from cyclic voltammetric analyses. Because of this modification the Pt(iv) prodrug achieved better physicochemical and pharmacological properties like water solubility and reduced toxicity for normal (non-cancerous) CHO cells respectively, as compared to cisplatin. Later, this Pt(iv) prodrug was loaded on 2-deoxy-d-glucose (2DG) functionalized over silica coated Fe3O4 magnetic nanoparticles (MNPs) to achieve the desired formulation. It exhibited potency as evidenced from the cytotoxicity evaluation against MCF-7 human breast cancer cell lines (IC50 ~ 14 μM). This encouraged us to further study the percentage viability, apoptosis and cell death evaluations on MCF-7, Colo-205 and CHO cells by flow cytometry. The cytotoxic potency of the formulation towards cancer cells, Colo-205 and MCF-7 (22-30% apoptosis), was revealed while the parent formulation was non-toxic to non-cancerous, CHO cell lines (3% apoptosis) as compared to cisplatin. It revealed that the formulation is comparable to cisplatin in its cell killing efficiency. Additionally the FITC labeled MNPs coated with 2DG exhibited efficient cell uptake and fast internalization (within 3 h) accumulating mainly in the cytoplasm and at the cell surface. Besides this, the formulation exhibited heating efficacy suggesting its possible application for hyperthermia treatment also. These results indicate the possible utility of the formulation for site specific delivery of the Pt(iv) prodrug of cisplatin. This journal is

A Synthetic Carbohydrate-Protein Conjugate Vaccine Candidate against Klebsiella pneumoniae Serotype K2

Ravinder, Mettu,Liao, Kuo-Shiang,Cheng, Yang-Yu,Pawar, Sujeet,Lin, Tzu-Lung,Wang, Jin-Town,Wu, Chung-Yi

, p. 15964 - 15997 (2020/11/13)

Klebsiella pneumoniae causes pneumonia and liver abscesses in humans worldwide and contains virulence factor capsular polysaccharides and lipopolysaccharides linked to the cell wall. Although capsular polysaccharides are good antigens for vaccine producti

Preparation method of glycyrrhetinic acid glucoside and application of glycyrrhetinic acid glucoside in sweetening agents

-

Paragraph 0007; 0015; 0018, (2020/07/29)

The invention relates to a synthetic route of glycyrrhetinic acid glucoside and application of glycyrrhetinic acid glucoside in sweetening agents, and belongs to the field of synthesis of novel sweetening agents. The novel sweetening agent with higher swe

Melophluosides A and B, new triterpene galactosides from the marine sponge Melophlus sarasinorum

Angkouw, Esther D.,Fukumoto, Arina,Hitora, Yuki,Ise, Yuji,Mangindaan, Remy E. P.,Sadahiro, Yusaku,Tsukamoto, Sachiko

, (2020/04/08)

Two new triterpene galactosides, melophluosides A and B, were isolated from a marine sponge Melophlus sarasinorum collected in Indonesia. Their structures were determined by the analysis of spectroscopic data and chemical reactions. The absolute configuration of cyclohexenone moiety was determined by the calculated ECD spectrum of a simplified model. Melophluosides A and B exhibited moderate cytotoxicity against HeLa cells (IC50, 11.6 and 9.7 μM, respectively).

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