14262-83-0

Usage

Uses

Used in Organic Chemistry:
2,3,4-tri-O-benzoylpentopyranosyl bromide is used as a synthetic intermediate for the preparation of complex carbohydrates and glycoconjugates. Its unique structure allows for the efficient synthesis of these biomolecules, which are essential for various biological processes.
Used in Medicinal Research:
In the pharmaceutical industry, 2,3,4-tri-O-benzoylpentopyranosyl bromide is utilized as a key building block for the development of carbohydrate-based drugs. Its ability to introduce carbohydrates into biomolecules makes it a valuable tool in the design and synthesis of novel therapeutic agents with potential applications in treating various diseases.
Used in Drug Synthesis:
2,3,4-tri-O-benzoylpentopyranosyl bromide is employed as a reactant in the synthesis of glycosidic bonds, which are crucial for the formation of various biologically active compounds. Its presence in the synthesis process ensures the formation of stable and functional glycosidic linkages, contributing to the development of effective drugs.
Used in Carbohydrate Chemistry:
In the field of carbohydrate chemistry, 2,3,4-tri-O-benzoylpentopyranosyl bromide serves as a versatile reagent for the modification and functionalization of carbohydrate structures. Its benzoyl-protected hydroxyl groups facilitate selective reactions, enabling the synthesis of diverse carbohydrate derivatives with tailored properties and applications.

Upstream product

• 372515-38-3 1',2',3',4'-tetra-O-benzoyl-L-lyxopyranose 
• 6763-34-4 D-xylose 
• 87-72-9 D-Xylose 
• 58-86-6 D-xylose 
• 618-32-6 Benzoyl bromide 
• 22435-09-2 1,2,3,4-tetra-O-benzoyl-β-D-xylopyranoside 
• 30319-44-9 1,2,3,4-tetra-O-benzoyl-α-D-xylopyranose 
• 10257-32-6 D-ribose 
• 909273-47-8 O²,O³,O⁴-Tribenzoyl-β-D-ribopyranose 
• 7473-43-0 tetra-O-benzoyl-β-D-ribopyranose 
• 98-88-4 benzoyl chloride 

Downstream Products

• 6638-76-2 methyl 2,3,4-tri-O-benzoyl-β-D-ribopyranoside 
• 34000-09-4 ethyl-(tri-O-benzoyl-β-D-ribopyranoside) 
• 7473-43-0 tetra-O-benzoyl-β-D-ribopyranose 
• 13035-46-6 benzyl-(tri-O-benzoyl-β-D-ribopyranoside) 
• 13035-43-3 tri-O-benzoyl-β-D-ribopyranosyl chloride 
• 19231-16-4 5-Chlor-3-<1'-(2',3',4'-tri-O-benzoyl-β-D-ribopyranosyl)>-2-benzoxazolon 
• 13035-48-8 tri-O-benzoyl-α-D-ribopyranosyl bromide 
• 909273-47-8 O²,O³,O⁴-Tribenzoyl-β-D-ribopyranose 
• 14218-06-5 tri-O-benzoyl-1,5-anhydro-ribitol 
• 13035-47-7 tri-O-benzoyl-α-D-ribopyranosyl chloride 
• 950762-02-4 4-formylphenyl (2,3,4-tri-O-benzoyl)-β-D-ribopyranoside 
• 1239883-54-5 propargyl 2,3,4-tri-O-benzoyl-β-D-ribopyranoside 
• 6638-76-2 1-O-methyl-2,3,4-O-tri-benzoyl-β-D-xylopyranoside 
• 35526-19-3 O²,O³,O⁴-Tribenzoyl-D-xylose 

Relevant academic research and scientific papers

Convergent strategy for the synthesis of S-linked oligoxylans

Arabinoxylans (AX) are a major class of hemicellulose and an important polysaccharide component of lignocellulosic biomass. To utilize the glycan polymer effectively, it is desirable to learn more about the enzymatic hydrolysis of AXs. Well-defined glycan

Delta-oleanolic acid saponin compound and medical application thereof

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

Total syntheses of schizandriside, saracoside and (±)-isolariciresinol with antioxidant activities

Lignans are widely distributed in plants and exhibit significant pharmacological effects, including anti-tumor and antioxidative activities. Here, we describe the total synthesis of schizandriside (1), a compound we previously isolated from Saraca asoca b

Total synthesis of agalloside, isolated from: Aquilaria agallocha, by the 5-O-glycosylation of flavan

Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic strategy holds promise for use in the synthesis of 5-O-glycosylated flavonoids. The synthesized agalloside (1) accelerated neural stem cell differentiation, which is a result comparable to that for the naturally occurring compound 1.

Stereoselective Epimerizations of Glycosyl Thiols

Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.

Synthesis of Functionalized 2-(4-Hydroxyphenyl)-3-methylbenzofuran Allosteric Modulators of Hsp90 Activity

Hsp90 is a molecular chaperone that plays a pivotal role in the cell life cycle. ATP-regulated internal dynamics are critical to Hsp90 function and we recently demonstrated that these dynamics can be modulated in an allosteric fashion; the protein C-terminal domain (CTD) can be effectively targeted with a family of 2-phenyl-benzofuran derivatives. Here we describe the expansion of the initial library, reporting 28 new derivatives that explore the chemical space at opposite ends of the benzofuran scaffold. Interactions of the compounds with a full-length protein homolog were explored by Saturation Transfer Difference (STD) NMR spectroscopy. In this context we also report the interaction epitope of Novobiocin, a known CTD inhibitor.

Synthesis, thermal properties, and cytotoxicity evaluation of hydrocarbon and fluorocarbon alkyl β-d-xylopyranoside surfactants

Alkyl β-d-xylopyranosides are highly surface active, biodegradable surfactants that can be prepared from hemicelluloses and are of interest for use as pharmaceuticals, detergents, agrochemicals, and personal care products. To gain further insights into th

Metal complexation of a D -ribose-based ligand decoded by experimental and theoretical studies

A combination of experimental and theoretical methods have been used to elucidate the complexation properties of a new sugar-derived hexadentate ligand, namely methyl 2,3,4-tri-O-(2-picolyl)-β-D-ribopyranoside (L). The coordination bond lengths in the complexes with MnII, Co II, NiII, and ZnII show substantial deviations from ideal octahedra with deformation towards trigonal-prismatic geometries, which is indicative of a conformationally constrained ligand. The metal-cation-ligand interactions were studied for L and the acyclic analogue L' [1,2,3-tri-O-(2-picolyl)-1,2,3-propanetriol] by spectroscopic methods and isothermal calorimetric titrations for the series MnII, Co II, NiII, ZnII, and CuII. The results indicate a stabilization of the complexes obtained with L compared with L', depending on the nature of the metal. Molecular modeling studies showed that the presence of the sugar moiety strongly favors conformations compatible with metal binding, which suggests an entropic origin of the stabilization of L complexes with regards to L' complexes. Moreover, the differences in the metal chelation profiles of L and L' are related to the constraints in the sugar group in the metal-bound structures. This study shows that foreseeing the degree of preorganization of flexible ligands may drive the design of a new generation of chelating compounds. A new sugar-derived ligand, with its coordination site embedded in a pyranoside cycle in the chair conformation, has been designed. Its transition-metal complexes were characterized by experimental and complexation methods and revealed a dramatic impact of the preorganization and complementarity of the carbohydrate scaffold on the metal binding.

Indium(III) triflate-mediated one-step preparation of glycosyl halides from free sugars

In(OTf)3 has been found to be an efficient catalyst for the direct conversion of reducing sugars to their respective acylated glycosyl halides in good yields under mild conditions. The glycosyl halides so obtained can be converted to alkyl glyc