132153-84-5

Basic information

• Product Name: 2-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate
• Synonyms: 2-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate;poly(glucosylethyl methacrylate)
• CAS NO: 132153-84-5
• Molecular Formula: C12H20O8
• Molecular Weight: 0
• Mol File: 132153-84-5.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 490.3°Cat760mmHg
• Flash Point: 184.2°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 1.14E-11mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: 2-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate(132153-84-5)
• EPA Substance Registry System: 2-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl 2-methylprop-2-enoate(132153-84-5)

Safety Data

• Hazardous Substances Data: 132153-84-5(Hazardous Substances Data)

Usage

Molecular structure

The compound consists of a complex sugar molecule (3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl and a 2-methylprop-2-enoate group.

Stereochemistry

The compound has a specific three-dimensional arrangement of atoms, with the R (rectus) configuration at the 3rd, 4th, 5th, and 6th carbon atoms of the sugar molecule.

Functional groups

The compound contains multiple hydroxyl (-OH) groups and a hydroxymethyl (-CH2OH) group in the sugar molecule, as well as an ester (-COO-) group connecting the sugar molecule to the 2-methylprop-2-enoate group.

Linkage

The sugar molecule is attached to the 2-methylprop-2-enoate group through an oxyethyl (-OCH2CH3) linkage.

Potential applications

The compound may have potential uses in pharmaceuticals, agriculture, or other industrial applications, although further research is needed to fully understand its properties and potential applications.

Complexity

The compound has a complex structure, which may contribute to its unique properties and potential uses.

Further research

The properties and potential uses of this chemical compound are not yet fully understood, and additional studies are necessary to explore its potential applications and benefits.

InChI:InChI=1/C12H20O8/c1-6(2)11(17)18-3-4-19-12-10(16)9(15)8(14)7(5-13)20-12/h7-10,12-16H,1,3-5H2,2H3/t7-,8-,9+,10-,12?/m1/s1

Upstream product

• 868-77-9 2-methyl-2-propenoic acid 2-hydroxyethyl ester 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 47703-15-1 2-O-((2',3',4',6'-tetra-O-acetyl)-β-D-galactosyl)hydroxyethyl methacrylate 
• 4163-60-4 β-D-galactose peracetate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 1190202-85-7 but-2-yn-1-yl β-D-galactopyranoside 
• 151168-59-1 1-propynyl-β-D-galactopyranoside 
• 74808-10-9 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)trichloroacetimidate 
• 7296-64-2 β-D-galactopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 15890-45-6 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucosyloxy)ethyl methacrylate 

Relevant articles and documents

Facile in situ preparation of biologically active multivalent glyconanoparticles

Biologically active multivalent glyconanoparticles are prepared in an extremely simple method by reduction of well-defined glycopolymers, prepared by RAFT polymerisation, in an aqueous solution of HAuCl4. The Royal Society of Chemistry 2006.

Chemo-enzymatic synthesis route to poly(glucosyl-acrylates) using glucosidase from almonds

Novel types of glucosyl-acrylate monomers are obtained by β-glucosidase from almond catalyzed glycosidation reaction. The saccharide-acrylate monomers were synthesized by reaction of d-glucose with hydroxyl functional acrylates: 2-hydroxyethyl acrylate (2

Enzymatic Synthesis of 2-(β-Galactosyl)-ethyl Methacrylate by β-Galactosidase from Pyrococcus woesei and Application for Glycopolymer Synthesis and Lectin Studies

Glycosidases have long been used for the synthesis of glycosides by transglycosylation reactions. Especially glycosidases from hyperthermophilic bacteria are useful for reactions under extreme reaction conditions, e.g., in the presence of organic solvents. We herein report the facile enzymatic synthesis and purification of 2-(β-galactosyl)-ethyl methacrylate (Gal-EMA) with the recombinant hyperthermostable glycosidase from Pyrococcus woesei in high yields. Optimized reaction conditions resulted in gram-scale synthesis of the galactosylated monomer with 88% transglycosylation yield. The product Gal-EMA was characterized by high-performance liquid chromatography-electrospray ionization-mass spectrometry (HPLC-ESI-MS), nuclear magnetic resonance (NMR) spectroscopy, and infrared (IR) spectroscopy. Gal-EMA was utilized to synthesize sugar-functionalized acrylate polymers with defined amounts of incorporated galactose (0-100%). Analysis of the binding affinity of the lectin RCA120 from Ricinus communis to the glycopolymers using an enzyme-linked lectin assay (ELLA) revealed KD values between 0.24 and 6.2 nM, depending on the amount of incorporated Gal-EMA. The potential of Gal-EMA for the synthesis of acrylate-functionalized glycan oligomers was demonstrated by sequential elongation of the terminal galactose by two glycosyltransferases, resulting in the terminal glycan N-acetyllactosamine (LacNAc) epitope. In conclusion, the enzymatic synthesis of Gal-EMA opens new routes to a series of novel monomeric building blocks for the synthesis of glycan-functionalized polyacrylates.

CARBOHYDRATE-BASED COMPOSITIONS AND METHODS FOR TARGETED DRUG DELIVERY

Provided herein are compositions and methods for intracellular delivery. The compositions are polymer compositions in which the polymer serves as a carrier for therapeutic and/or diagnostic agents. The polymer compositions are effective in targeted delivery of therapeutic and/or diagnostic agents to a cell. The polymer compositions include a targeting moiety that includes carbohydrate groups that effectively target specific cell surface receptors. The polymer compositions also include an agent binding moiety that effectively associates the therapeutic and/or diagnostic agent to be delivered to the cell.