40690-74-2

Usage

Uses

1. Used in Polymer Synthesis:
1,2:5,6-di-O-isopropylidene-3-O-acrylate-α-D-glucopentoaldo-1,4-furanose is used as a monomer for the synthesis of well-defined glycopolymers. The presence of the acrylate group allows for controlled radical polymerization techniques such as NMP, RAFT, or ATRP to be employed, resulting in glycopolymers with specific properties and applications.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2:5,6-di-O-isopropylidene-3-O-acrylate-α-D-glucopentoaldo-1,4-furanose can be used as a building block for the development of novel drug delivery systems. The synthesized glycopolymers can be tailored to target specific diseases or conditions, improving the efficacy and bioavailability of therapeutic agents.
3. Used in Biomedical Applications:
1,2:5,6-di-O-isopropylidene-3-O-acrylate-α-D-glucopentoaldo-1,4-furanose can be utilized in the development of biomaterials for tissue engineering and regenerative medicine. The synthesized glycopolymers can mimic the natural extracellular matrix, promoting cell adhesion, proliferation, and differentiation.
4. Used in Material Science:
In material science, 1,2:5,6-di-O-isopropylidene-3-O-acrylate-α-D-glucopentoaldo-1,4-furanose can be used to create novel materials with unique properties, such as hydrogels, coatings, and films. These materials can find applications in various fields, including sensors, drug delivery, and environmental remediation.
5. Used in Food Industry:
1,2:5,6-di-O-isopropylidene-3-O-acrylate-α-D-glucopentoaldo-1,4-furanose can be employed in the food industry for the development of functional ingredients, such as prebiotics, texturizers, and stabilizers. The synthesized glycopolymers can enhance the nutritional value, texture, and shelf life of food products.

Upstream product

• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 814-68-6 acryloyl chloride 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2051-76-5 acrylic acid anhydride 
• 20316-77-2 (3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole 
• 2280-44-6 D-Glucose 
• 121-69-7 N,N-dimethyl-aniline 
• 530-26-7 D-Mannose 
• 79-10-7 acrylic acid 

Downstream Products

• 89845-61-4 1,2:5,6-Di-O-isopropylidene-3-O-<3-(5-fluorouracil-1-yl)propionyl>-α-D-glucofuranose 
• 83320-32-5 1,2:5,6-di-O-isopropylidene-3-O-<3-(uracil-1-yl)propionoyl>-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 

Relevant academic research and scientific papers

Asymmetric Baylis-Hillman reaction using sugar acrylates - Synthesis of optically active α-methylene-β-hydroxy alkanoates

A study on the asymmetric Baylis-Hillman reaction of three chiral acrylates; 1,2:5,6-di-O-iso-propylidine-α-D-glucofuranose-3-acrylate 1, 2,3:5,6-di-O-iso-propylidine-α-D-mannofuranose-1-acrylate 2 and 1,2-O-iso-propylidine-5-O-tert-butyldimethylsilyl-α-D-xylofuranose-3 -acrylate 3, with various aldehydes was conducted, resulting in adducts with moderate diastereoselectivity (5-40% e.e.).

Monoacryloyl esters of carbohydrates: Synthesis, polymerization and application in ceramic technology

The article presents the interdisciplinary research among organic synthesis, chemistry of polymers and ceramic technology. It presents the synthesis of monoacryloyl esters of fructose and glucose that is 1-O-acryloyl-d-fructose and 3-O-acryloyl-d-glucose,

Tetrabutylammonium peroxydisulfate in organic synthesis; XI.1 A novel and selective approach to the oxidative deprotection of allyl ethers with tetrabutylammonium peroxydulfate

A tetrabutylammonium peroxydisulfate-mediated oxidative procedure for the mild selective deprotection of allyl ethers to form the corresponding alcohols is described. The alcohols are obtained in yields of 81-85% and the method is compatible with several functional groups under these reaction conditions.

Synthesis of hyperbranched glycopolymers via self-condensing atom transfer radical copolymerization of a sugar-carrying acrylate

Hyperbranched glycopolymers were synthesized by self-condensing vinyl copolymerization (SCVCP) of an acrylic AB* inimer, 2-(2-bromopropionyloxy)ethyl acrylate (BPEA), with 3-O-acryloyl-1,2: 5,6-di-O-isopropylidene-α-D-glucofuranoside (AIGlc) via atom transfer radical polymerization (ATRP), followed by deprotection of the isopropylidene protecting groups. Homopolymerization of AIGlc with the CuBr/pentamethyldiethylenetriamine (PMDETA) catalyst system in solution resulted in linear poly(AIGlc) having controlled molecular weights and narrow molecular weight distribution, which were characterized using GPC, GPC/viscosity, and MALDI-TOF mass spectrometry. The catalyst system could be applied for SCVCP to synthesize hyperbranched poly(AIGlc)s, in which the molecular weights, the composition of AIGlc segment, and the branched structures can be adjusted by an appropriate choice of the comonomer ratio, γ. Deprotection of the isopropylidene protecting groups of the branched poly(AIGlc)s resulted in water-soluble glycopolymers with randomly branched architectures.

NANOPARTICLES FOR DRUG-DELIVERY

This invention relates to a unique process for the preparation of polymeric nanoparticles with target molecules bonded to the surface of the particles and having sizes of up to 1000nm, preferably Inm to 400nm, more preferably Inm to 200nm, that are dispersed homogeneously in aqueous solution. To accomplish the above objective, the polymeric nanoparticles of the subject invention are prepared using a novel technique of microemulsion polymerization. The resulting aqueous solution of polymeric nanoparticles is comprised of about 1 to 100 parts per weight of water or buffer, about 1 to 80 parts per weight of polymeric nanoparticles, which the bio-active molecules are conjugated, about 0.001 to 10 parts per weight of emulsifier, and about 0.00001 to 5 parts per weight of radical initiator based on the weight of the solution. In the method of this invention, the target drug/target substance is covalently bonded to the polymeric nanoparticles to secure them from outer intervention in vivo or cell culture in vitro until they are exposed at the target site within the cell.

Synthesis of Copolymers of Vinylpyrrollidone with Monosubstituted Esters of Carbohydrates and Unsaturated Carboxylic Acids

Monoesters of diisopropylidene glucose with crotonic, methacrylic, and acrylic acids and of diisopropylidene mannose and sorbose with crotonic acid were prepared.Copolymers of these monomers with vinylpyrrolidone, containing up to 20 mol percent carbohydrate-containing units, were prepared by radical copolymerization.Kinetics of removal of protecting isopropylidene groups was studied by 1H NMR spectroscopy.

New carbohydrate-based chiral auxiliaries in Diels-Alder reaction

The carbohydrate derivatives 1-5 were evaluated as chiral auxiliaries in the Diels-Alder reaction of its acrylate derivatives 6a-e with cyclopentadiene promoted by Lewis acids. Although excellent endo:Exo ratios (98:2) were obtained in many cases, the π-facial selectivities were from low to moderate (up to 60% d.e.). An effect of non-coordinating solvents reversing the stereoselectivities of adducts obtained from acrylates 6a,b was also found.

Synthesis of Polymerizable Hexose Derivatives

Polymerizable esters of methacrylic and acrylic acid with di-O-isopropylidenehexoses as alcohol components have been synthesized.

SILYL NITRONATES AND NITRILE OXIDES IN ORGANIC SYNTHESIS. A NOVEL ROUTE TO D,L-DEOXYSUGARS. USE OF ALUMINIUM OXIDE AS SOLID PHASE BASE FOR GENERATION OF NITRILE OXIDES FROM HYDROXIMIC ACID CHLORIDES

Novel methodology is developed for a three step synthesis of deoxyaldoses and deoxyketoses. 1.Regioselective addition of silyl nitronate or nitrile oxide to a diene. 2.Stereospecific hydroxylation of the double bond. 3.Unmasking of the aldol moiety by catalytic reduction of the 2-isoxazoline.The syntheses of D.L-deoxyribose, D,L-oleose, D,L-digitoxose, D,L-2-deoxygalactose, 1,3-dideoxyfructose, 3-deoxyfructose etc. are described.Basic aluminium oxide is introduced as a solid phase base for the one step synthesis of 2-isoxazolines from aldoximes and olefins.An X-ray diffraction study of compound 13c verifies the stereochemical assignments.