6638-76-2

Basic information

• Product Name: methyl 2,3,4-tri-O-benzoylpentopyranoside
• CAS NO: 6638-76-2
• Molecular Formula: C₂₇H₂₄O₈
• Molecular Weight: 476.4747
• Mol File: 6638-76-2.mol

Chemical Properties

• Boiling Point: 613.7°C at 760 mmHg
• Flash Point: 262.5°C
• Density: 1.32g/cm³
• Vapor Pressure: 5.39E-15mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: methyl 2,3,4-tri-O-benzoylpentopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4-tri-O-benzoylpentopyranoside(6638-76-2)
• EPA Substance Registry System: methyl 2,3,4-tri-O-benzoylpentopyranoside(6638-76-2)

Safety Data

• Hazardous Substances Data: 6638-76-2(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 91-09-8 (2S,3S,4R,5R)-2-Methoxy-tetrahydro-pyran-3,4,5-triol 
• 67-56-1 methanol 
• 40010-17-1 2,3,4-tri-O-benzoyl-β-D-arabinopyranosyl bromide 
• 30319-42-7 1,2,3,4-tetra-O-benzoyl-α-D-arabinopyranose 
• 22434-99-7 1,2,3,4-tetra-O-benzoyl-β-D-arabinopyranose 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 122999-79-5 O¹,O³,O⁵-tribenzoyl-O²-methanesulfonyl-β-D-arabinofuranose 
• 110-86-1 pyridine 
• 124-41-4 sodium methylate 
• 91-09-8 methyl β-D-ribopyranoside 
• 13035-44-4 2,3,4-tri-O-benzoyl-β-D-ribopyranosyl bromide 
• 13035-48-8 tri-O-benzoyl-α-D-ribopyranosyl bromide 
• 74-88-4 methyl iodide 

Downstream Products

• 91-09-8 (2S,3S,4R,5R)-2-Methoxy-tetrahydro-pyran-3,4,5-triol 
• 102448-76-0 methyl-(O³,O⁴-dibenzoyl-O²-methanesulfonyl-α-D-arabinopyranoside) 
• 4782-99-4 methyl-(O³,O⁴-isopropyliden-α-D-arabinopyranoside) 
• 50447-01-3 methyl 2-O-methanesulfonyl-α-D-arabinopyranoside 
• 863998-29-2 methyl 3,4-O-isopropylidene-2-O-methanesulfonyl-α-D-arabinopyranoside 
• 91-09-8 methyl β-D-ribopyranoside 

Relevant articles and documents

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.

Sinularioside, a triacetylated glycolipid from the Indonesian soft coral Sinularia sp., is an inhibitor of NO release

Chemical analysis of the Indonesian soft coral Sinularia sp. (order Alcyonacea, family Alcyoniidae) afforded a known glucosylcerebroside of the sarcoehrenoside-type and sinularioside (2), a new naturally triacetylated glycolipid containing two α-d-arabinopyranosyl residues and a myristyl alcohol unit. Their complete stereostructures were solved by interpretation of MS and NMR data along with CD analysis of degradation products. Sinularioside proved to moderately inhibit LPS-induced NO release, providing interesting clues into the poorly understood structure-activity relationships for anti-inflammatory glycolipids.

Novel D-xylose derivatives stimulate muscle glucose uptake by activating AMP-activated protein kinase α

Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myot

Vesparioside from the marine sponge Spheciospongia vesparia, the first diglycosylceramide with a pentose sugar residue

The marine sponge Spheciospongia vesparia produces vesparioside (1a), a diglycosylated glycosphingolipid which is the first example of a natural diglycosylceramide with a pentose sugar residue. The structure of vesparioside was mostly determined by extensive spectroscopic analysis but determination of the nature of the alkyl chains and elucidation of the absolute stereochemistry of the sugars and of the ceramide required chemical degradation. In this respect, an improved and simplified procedure for the microscale chemical degradation of glycosphingolipids was employed here for the first time. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

On the Role of Neighboring Group Participation and Ortho Esters in β-Xylosylation: 13C NMR Observation of a Bridging 2-Phenyl-1,3-dioxalenium Ion

The role of ortho esters in the formation of 2,3,4-tri-O-benzoyl-β-xylopyranosides from various donor/ promoter pairs has been investigated. It is concluded that for the activation of sulfoxides with Tf2O, thioglycosides with PhSOTf, and bromides with AgOTf the anomeric configuration of the donor is of no consequence on the outcome of the reaction. In all methods studied, the presence or absence of a non-nucleophilic, hindered base is of crucial importance with ortho esters only being discernible in its presence. S-Phenyl 2,3,4-tri-O-benzoyl-1-deoxy-1-thia-β-D-xylopyranoside was synthesized enriched with 13C at each of the three carbonyl carbons. Activation of this thioglycoside with PhSOTf in CD2Cl2 at -78 °C with or without the base permits, for the first time, the observation by 13C NMR spectroscopy of a bridging dioxalenium ion as an intermediate in a neighboring group directed glycosylation. Quenching of this cation in the presence of the base leads to the ortho ester, whereas in the absence of the base the glycosides are the only products detected.

Lithium aluminium hydride reduction of glycopyranoside-monosulfonates: Formation of branched furanosides

Lithium aluminum hydride reduction of glycopyranoside-monotosylates caused three reactions: (1) stereospecific 1,2-shift, producing branched furanosides (path A), (2) reductive O-S bond cleavage, producing the original glycosides (path B), and (3) reductive removal of the tosyloxy group, producing deoxyglycosides (path C). The path A reaction was particularly evident for the monotosylates at 2-O, 3-O, and 4-O: for example, methyl 2-O-tosyl-α-D-xylopyranoside gave methyl 2-deoxy-2-C-(hydroxymethyl)-α-D-α-erythrofuranoside in 60% yield. This reaction opens a new and efficient route to branched glycofuranosides of natural and unnatural type. Stereo-electronic requirements of this reaction in relation to the balance of the other two reactions are discussed.