84563-90-6

Basic information

• Product Name: 1,2-O-(1-Methylethylidene)-3-O-(phenylMethyl)-, 6-acetate 5-Methanesulfonate-a-D-Glucofuranose
• Synonyms: 1,2-O-(1-Methylethylidene)-3-O-(phenylMethyl)-, 6-acetate 5-Methanesulfonate-a-D-Glucofuranose;1,2-O-(1-Methylethylidene)-3-O-(phenylmethyl)-alpha-D-glucofuranose 6-acetate 5-methanesulfonate
• CAS NO: 84563-90-6
• Molecular Formula: C₁₉H₂₆O₉S
• Molecular Weight: 430.46934
• Mol File: 84563-90-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-O-(1-Methylethylidene)-3-O-(phenylMethyl)-, 6-acetate 5-Methanesulfonate-a-D-Glucofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-O-(1-Methylethylidene)-3-O-(phenylMethyl)-, 6-acetate 5-Methanesulfonate-a-D-Glucofuranose(84563-90-6)
• EPA Substance Registry System: 1,2-O-(1-Methylethylidene)-3-O-(phenylMethyl)-, 6-acetate 5-Methanesulfonate-a-D-Glucofuranose(84563-90-6)

Safety Data

• Hazardous Substances Data: 84563-90-6(Hazardous Substances Data)

Usage

Chemical structure

A furanose sugar molecule with modifications

Explanation

The compound is based on a furanose sugar, which is a type of monosaccharide with a five-membered ring structure.

Explanation

A 1-methylethylidene group (also known as an isopropylidine group) is a three-carbon substituent that is attached to the first carbon of the furanose sugar.

Explanation

A phenylmethyl group (also known as a benzyl group) is a phenyl group attached to a methyl group, which is attached to the third carbon of the furanose sugar.

Explanation

An acetate group is a derivative of acetic acid, which is attached to the sixth carbon of the furanose sugar, indicating an ester linkage.

Explanation

A methanesulfonate group is a methane with a sulfonic acid group (-SO3H) attached, which is connected to the fifth carbon of the furanose sugar.

Explanation

The compound has an alpha (a) configuration and is derived from D-glucose, a common monosaccharide. The furanose ring structure is based on D-glucofuranose.

Explanation

Due to its unique chemical structure and properties, the compound may have potential uses in various fields, but further research and analysis are required to understand its full potential.

Explanation

The compound's potential applications and effects on biological systems or chemical reactions are not yet fully understood and require additional study.

1-Methylethylidene group

Attached to the 1st carbon

Phenylmethyl group

Attached to the 3rd carbon

Acetate group

Attached to the 6th carbon

Methanesulfonate group

Attached to the 5th carbon

Stereochemistry

a-D-Glucofuranose

Potential applications

Pharmaceutical, agrochemical, or industrial processes

Need for further research

To understand potential uses and effects

Upstream product

• 22331-19-7 3-O-benzyl-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose 
• 127-08-2 potassium acetate 
• 127-09-3 sodium acetate 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 124-63-0 methanesulfonyl chloride 
• 177897-25-5 6-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18006-25-2 3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose diacetate 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 

Downstream Products

• 37776-17-3 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 5531-09-9 3-O-benzyl-L-idopyranose 
• 118711-49-2 1,2,4,6-tetra-O-acetyl-3-O-benzyl-L-idopyranoside 
• 781657-63-4 phenyl 3-O-benzyl-1-thio-L-idopyranoside 
• 781657-64-5 (2R,4aS,7R,8R,8aR)-8-Benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 781657-65-6 Acetic acid (2R,4aS,7R,8S,8aR)-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 781657-62-3 phenyl 2,4,6-tri-O-acetyl-1-thio-α/β-L-idopyranose 
• 42926-89-6 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose 

Relevant articles and documents

Synthesis of heparin oligosaccharides and their interaction with eosinophil-derived neurotoxin

A convenient route for the synthesis of heparin oligosaccharides involving regioselective protection of d-glucosamine and a concise preparation of rare l-ido sugars from diacetone α-d-glucose is described. Stereoselective coupling of a d-glucosamine-derived trichloroacetimidate with a 1,6-anhydro-β-l-idopyranosyl 4-alcohol gave the desired α-linked disaccharide, which was used as repeating unit for dual chain elongation and termination. Stepwise assembly from the reducing to the non-reducing end with a d-glucosamine-derived monosaccharide as starting unit furnished the oligosaccharide skeletons having different chain lengths. A series of functional group transformations afforded the expected heparin oligosaccharides with 3, 5 and 7 sugar units. Interaction of these oligosaccharides with eosinophil-derived neurotoxin (EDN), a cationic ribonuclease and a mediator produced by human eosinophils, was further investigated. The results revealed that at 5 μg mL-1, the heptasaccharide has sufficiently strong interference to block EDN binding to Beas-2B cells. The tri- and pentasaccharides have moderate inhibitory properties at 50 μg mL-1 concentration, but no inhibition has been observed at 10 μg mL-1. The IC50 values of the tri-, penta- and heptasaccharides are 69.4, 47.2 and 0.225 μg mL-1, respectively.

Synthesis of a polysulfated heparin degradation product

Two suitable methods for the synthesis of the heparin degradation product 2,5-anyhydro-3-O-(α-L-ido-pyranosyluronate)-D-mannitol hexa O-sulfate are reported. The synthesis pathways start from D-glucose and D-glucosamine.

SYNTHESIS OF SOME L-IDOSE DERIVATIVES

The synthesis of 3-O-benzyl and 3-O-mesyl-1,2-O-isopropylidene-β-L-idofuranose has been effected on the basis of the intramolecular nucleophilic exchange of a mesyloxy group at C5 in derivatives of 1,2-O-isopropylidene-α-D-glucofuranose.It has