2715-35-7

Usage

Chemical structure

A synthetic chemical compound derived from the sugar galactose, with two isopropylidene groups and an acryloyl group attached to the carbon atoms at positions 1, 2, 3, 4, and 6 of the galactose ring.

Application

Commonly used in organic chemistry reactions and synthesis, particularly in carbohydrate chemistry research.

Functional group

The presence of the acryloyl group allows for further modification and functionalization of the molecule.

Protection

The isopropylidene groups serve to protect the reactive hydroxyl groups on the sugar, making it a useful building block in organic synthesis.

Unique structure

Its unique structure and properties make it a valuable tool in the development of new molecules and materials.

Stereochemistry

Retains the α-D-galactopyranose configuration, which is important for its reactivity and potential applications in carbohydrate chemistry.

Solubility

Typically soluble in organic solvents such as chloroform, dichloromethane, and acetone, which facilitates its use in various chemical reactions.

Stability

Relatively stable under normal laboratory conditions, but should be stored away from light and moisture to prevent degradation.

Synthesis

Can be synthesized through a series of chemical reactions, starting from the parent sugar galactose and introducing the isopropylidene and acryloyl groups.

Purity

High purity is essential for its use in research and synthesis, as impurities can affect the outcome of chemical reactions and the properties of the final product.

Upstream product

• 10257-28-0 D-Galactose 
• 814-68-6 acryloyl chloride 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 

Relevant academic research and scientific papers

Synthesis, characterization, and biological interaction of glyconanoparticles with controlled branching

Branched amphiphilic copolymers were synthesized through the reversible addition - fragmentation chain transfer (RAFT) chain extension of a poly(methyl acrylate) macro-chain transfer agent using a protected galactose monomer and a polymerizable chain transfer agent branching unit. After galactose deprotection, the copolymers were self-assembled via nanoprecipitation. The resultant nanoparticles were analyzed for their size, shape, and biological interaction with a galactose binding lectin. Using light scattering, the nanoparticles were determined to be solid spheres. Nanoparticles containing branched glycoblocks bound significantly more lectin than those containing comparable linear blocks. By adjusting the molecular weight and branching of the copolymer, the size of the self-assembled nanoparticle and the saccharide density on its surface can be varied. (Figure Presented).

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.

Visible-Light-Induced Trifluoromethylation of Allylic Alcohols

An organic photoredox-catalyzed dehydroxylative trifluoromethylation of allylic alcohols was developed in an environmentally benign manner. In this reaction, the readily available CF3SO2Na was selected as the trifluoromethylation reagent. The in situ generated byproduct SO2 was reutilized to activate C-OH bond, which enabled this dehydroxylative trifluoromethylation to be performed conveniently. A variety of multifunctionalized CF3-allylic compounds were obtained in high yields and excellent stereoselectivity.

Trifluoromethyl allyl compound as well as preparation method and application thereof

The invention discloses a trifluoromethyl allyl compound as well as a preparation method and application thereof. According to the method, allyl alcohol is directly used as a raw material, CF3SO2Na is selected as a trifluoromethylation reagent, a metal-free and cheap photooxidation reduction catalyst is used, and under the catalysis of an organic photooxidation reduction agent, a byproduct SO2 generated in situ is reused as an activated C-OH bond, so that the reaction is carried out in an environment-friendly manner under a mild condition. The allyl alcohol used in the preparation method disclosed by the invention is a MoritA-Baylis-Hillman alcohol allyl alcohol raw material which is simple to synthesize and high in conversion rate, the applicable substrate range is wide, and the preparation cost is low. In addition, the preparation method disclosed by the invention is simple in steps, and has the characteristics of convenience in operation, environment friendliness, excellent stereoselectivity and broad-spectrum functional group tolerance. The trifluoromethyl allyl compound provided by the invention is a general precursor for preparing related CF3 molecules, has potential pharmaceutical activity and biological activity, and can be widely applied to biological and pharmaceutical active molecules.

Late-Stage Macrocyclization of Bioactive Peptides with Internal Oxazole Motifs via Palladium-Catalyzed C-H Olefination

Oxazole is an important pharmacophore and exists in the backbone of many bioactive peptide natural products and peptidomimetics. Efficient methods for the synthesis and direct functionalization of complex oxazole-containing peptides are in high demand. Herein, we report the late-stage site-selective functionalization of oxazole-containing peptides via palladium-catalyzed δ-C(sp2)-H olefination of phenylalanine, tryptophan, and tyrosine residues. This strategy utilizes oxazole motifs as internal directing groups and provides access to oxazole-containing peptide macrocycles with bioactivities.

Drug and Imaging Agent Delivery Compositions and Methods

A multi-arm, star-shaped polymer composition can be configured for drug delivery and imaging applications in vivo. The star polymer architecture can be synthesized using living radical polymerization techniques, including reversible addition-fragmentation chain transfer and macromolecular design via the interchange of xanthates with a broad range of reaction conditions and functional groups. The star-shaped polymeric carriers can be tailored for preferential delivery of chemotherapeutics into the tumor-draining lymphatics via subcutaneous, peritumoral or intratumoral injections. The carriers can be loaded with the chemotherapeutic agents from about 10% to about 25% w/w. In addition, the carriers can be loaded with imaging agents from about 5% to about 10% w/w. The molecular weights of the polymeric carriers can be about 40 kDa to about 130 kDa. The chemotherapeutics can be cisplatin, geldanamycin or nitric oxide-donating prodrugs. The imaging agent can be a near-infrared dye, such as IR820.

A unique aliphatic tertiary amine chromophore: Fluorescence, polymer structure, and application in cell imaging

Although photoluminescence of tertiary aliphatic amines has been extensively studied, the usage of this fundamental chromophore as a fluorescent probe for various applications has unfortunately not been realized because their uncommon fluorescence is easily quenched, and strong fluorescence has been observed only in vapor phase. The objective of this study is how to retain the strong fluorescence of tertiary amines in polymers. Tertiary amines as branching units of the hyperbranched poly(amine-ester) (HypET) display relatively strong fluorescence (Φ = 0.11-0.43). The linear polymers with tertiary amines in the backbone or as the side group are only very weakly fluorescent. The tertiary amine of HypET is easily oxidized under ambient conditions, and red-shifting of fluorescence for the oxidized products has been observed. The galactopyranose-modified HypET exhibits low cytotoxicity and bright cell imaging. Thus, this study opens a new route of synthesizing fluorescent materials for cell imaging, biosensing, and drug delivery.

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.