39541-20-3

Usage

Uses

Used in Carbohydrate Chemistry:
Azido 2-AcetaMido-2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranosyl is used as a synthetic intermediate for the preparation of complex carbohydrate structures. Its unique chemical properties allow for the creation of diverse molecules with potential applications in various fields.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Azido 2-AcetaMido-2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranosyl is used as a key building block for the development of novel drugs targeting various diseases. Its ability to form complex carbohydrate structures makes it a valuable asset in the design and synthesis of potential therapeutic agents.
Used in Research and Development:
Azido 2-AcetaMido-2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranosyl is also utilized in research and development settings, where it aids in the study of carbohydrate-based interactions and the development of new methodologies for carbohydrate synthesis. This contributes to a deeper understanding of carbohydrate biology and the potential for new discoveries in the field.
Used in Material Science:
In the field of material science, Azido 2-AcetaMido-2-deoxy-3,4,6-tri-O-acetyl-β-D-galactopyranosyl can be employed in the design and synthesis of carbohydrate-based materials with unique properties. These materials may have applications in areas such as drug delivery, sensors, and biocompatible coatings.

Upstream product

• 39541-21-4 1-bromo-2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-β-D-galactopyranoside 
• 76375-60-5 (3R,4R,5R,6R)-3-acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate 
• 14257-79-5 β-D-galactosamine hydrochloride 
• 1772-03-8 D-(+)-galactosamine hydrochloride 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-galactopyranose 
• 41355-44-6 2-acetamido-2,4,6,-tri-O-acetyl-1-chloro-1,2-dideoxy-α-D-galactopyranose 
• 133964-95-1 Acetic acid (2R,3R,4R,5R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-bromo-tetrahydro-pyran-4-yl ester 

Downstream Products

• 39541-22-5 (2R,3R,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-aminotetrahydro-2H-pyran-3,4-diyl diacetate 

Relevant academic research and scientific papers

Synthesis and Evaluation of New Trivalent Ligands for Hepatocyte Targeting via the Asialoglycoprotein Receptor

Since the asialoglycoprotein receptor (also known as the Ashwell-Morell receptor or ASGPR) was discovered as the first cellular mammalian lectin, numerous drug delivery systems have been developed and several gene delivery systems associated with multivalent ligands for liver disease targeting are undergoing clinical trials. The success of these systems has facilitated the further study of new ligands with comparable or higher affinity and less synthetic complexity. Herein, we designed two novel trivalent ligands based on the esterification of tris(hydroxymethyl) aminomethane (TRIS) followed by the azide-alkyne Huisgen cycloaddition with azido N-acetyl-d-galactosamine. The presented triazolyl glycoconjugates exhibited good binding to ASGPR, which was predicted using in silico molecular docking and assessed by a surface plasmon resonance (SPR) technique. Moreover, we demonstrated the low level of in vitro cytotoxicity, as well as the optimal spatial geometry and the required amphiphilic balance, for new, easily accessible ligands. The conjugate of a new ligand with Cy5 dye exhibited selective penetration into HepG2 cells in contrast to the ASGPR-negative PC3 cell line.

A One-Pot approach to neoglycopeptides using orthogonal native chemical ligation and click chemistry

The powerful combination of native chemical ligation and click chemistry has been used to affect a one-pot synthesis of neogiycopeptiaes from propargyl-containing peptides using GaINAc-N3 as the glycan component. A versatile chemical toolkit fo

Impact of Phosphorothioate Chirality on Double-Stranded siRNAs: A Systematic Evaluation of Stereopure siRNA Designs

Oligonucleotides are important therapeutic approaches, as evidenced by recent clinical successes with antisense oligonucleotides (ASOs) and double-stranded short interfering RNAs (siRNAs). Phosphorothioate (PS) modifications are a standard feature in the

Synthesis, Characterization, X-Ray Crystallography, and Antileishmanial Activities of N-Linked and O-Linked Glycopyranosides

Novel N-linked 5a-e and O-linked glycopyranosides 7a-e were synthesized in high yield from commercially available L-tartaric acid containing two asymmetric centers and C2 axis of symmetry. The compound L-tartaric acid was completely protected and then partially hydrolyzed to get the monoester, which upon treatment with different amino and hydroxyl derivatives of glycopyranoses gave the desired amides and esters. The synthesized derivatives were purified by chromatography and characterized by spectroanalytical techniques. The structure of compound 7c in the series was supported by X-ray analysis. Leishmanicidal activities of compounds 5a-e and 7a-e were investigated which showed moderate to good activities.

POLYNUCLEOTIDE CONSTRUCTS

Disclosed are polynucleotide constructs having a strand linked to a moiety carrying one or more auxiliary moieties. Also disclosed are polynucleotide constructs interrupted with a sugar analogue, and polynucleotide constructs with stereochemical^ enriched phosphorothioates. The polynucleotide constructs may be provided as hybridized polynucleotide constructs. Also featured are methods of delivery a polynucleotide construct to a cell and methods of reducing the expression of a protein in a cell by contacting the cell with the disclosed polynucleotide construct or hybridized polynucleotide construct.

POLYNUCLEOTIDE CONSTRUCTS HAVING AN AUXILIARY MOIETY NON-BIOREVERSIBLY LINKED TO AN INTERNUCLEOSIDE PHOSPHATE OR PHOSPHOROTHIOATE

The invention features a hybridized polynucleotide construct including a passenger strand, a guide strand loadable into a RISC complex, and one or more auxiliary moieties. At least one of the auxiliary moieties is non-bioreversibly linked to an internucleoside phosphate or phosphorothioate in the passenger strand. The invention further features methods of delivery a polynucleotide construct to a cell and methods of reducing the expression of a protein in a cell. The methods typically involve contacting the cell with the hybridized polynucleotide construct.

OLIGONUCLEOTIDE-LIGAND CONJUGATES AND PROCESS FOR THEIR PREPARATION

The present invention relates to ligand conjugates of oligonucleotides (e.g., iRNA agents) and methods for their preparation. The ligands are derived primarily from monosaccharides These conjugates are useful for the in vivo delivery of oligonucleotides.

POLYNUCLEOTIDE CONSTRUCTS HAVING BIOREVERSIBLE AND NON-BIOREVERSIBLE GROUPS

The invention features a hybridized polynucleotide construct containing a passenger strand, a guide strand loadable into a RISC complex, and (i) a 3'-terminal or an internucleotide non-bioreversible group in the guide strand; or (ii) a 5'-terminal, a 3'-terminal, or an internucleotide non-bioreversible group in the passenger strand, and a 5'-terminal, a 3'-terminal, or an internucleotide disulfide bioreversible group in the guide strand or the passenger strand. The invention also features methods of delivering a polynucleotide to a cell using the hybridized polynucleotide construct. The invention further features methods of reducing the expression of a polypeptide in a cell using the hybridized polynucleotide construct.

Regiospecific anomerisation of acylated glycosyl azides and benzoylated disaccharides by using TiCl4

Chelation induced anomerisation is promoted when Lewis acids, such as TiCl4 or SnCl4, coordinate to the pyranose ring oxygen atom and another site, giving rise to endocyclic cleavage and isomerisation to the more stable anomer. In this research regiospecific site-directed anomerisation is demonstrated. TiCl4 (2.5equiv) was employed to induce anomerisation of 15 glycosyl azide and disaccharide substrates of low reactivity, and high yields (>75 %) and stereoselectivies (α/β>9:1) were achieved. The examples included glucopyranuronate, galactopyranuronate and mannopyranuronate as well as N-acetylated glucopyranuronate and galactopyranuronate derivatives. A disaccharide with the α1→4 linkage found in polygalacturonan was included. The use of benzoylated saccharides was found to be important in disaccharide anomerisation as attempts to isomerise related acetyl protected and 2,3-carbonate protected derivatives were not successful. Copyright