4098-06-0

Usage

Uses

Used in Pharmaceutical Industry:
3,4,6-Tri-O-acetyl-D-galactal is used as a key intermediate for the synthesis of various pharmaceutical compounds, particularly those involving oligosaccharides. Its role in the creation of these complex carbohydrates is crucial for the development of new drugs and therapies.
Used in Chemical Research:
In the field of chemical research, 3,4,6-Tri-O-acetyl-D-galactal is used as a starting material for the synthesis of a wide range of complex organic compounds. Its unique structure allows researchers to explore new reactions and develop novel chemical pathways.
Used in Material Science:
3,4,6-Tri-O-acetyl-D-galactal is also utilized in material science for the development of new materials with specific properties. Its ability to form oligosaccharides can be harnessed to create materials with unique characteristics, such as improved biocompatibility or enhanced mechanical properties.
Used in Food Industry:
In the food industry, 3,4,6-Tri-O-acetyl-D-galactal can be used as a component in the development of new food additives or ingredients. Its role in the synthesis of oligosaccharides can lead to the creation of novel compounds with specific flavors, textures, or nutritional benefits.
Overall, 3,4,6-Tri-O-acetyl-D-galactal is a versatile compound with a wide range of applications across various industries, including pharmaceuticals, chemical research, material science, and the food industry. Its importance as a building block for the synthesis of oligosaccharides makes it a valuable asset in the development of new products and technologies.

InChI:InChI=1/C12H16O7/c1-7(13)17-6-11-12(19-9(3)15)10(4-5-16-11)18-8(2)14/h4-5,10-12H,6H2,1-3H3/t10-,11-,12-/m1/s1

Upstream product

• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 59-23-4 D-Galactose 
• 116050-49-8 2-pyridyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-D-lyxo-hexopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 108-24-7 acetic anhydride 
• 21193-75-9 D-galactal 
• 75-36-5 acetyl chloride 
• 14227-87-3 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl chloride 
• 107-13-1 acrylonitrile 
• 14227-54-4 2,3,4,6-tetra-O-acetyl-α-D-talopyranosyl bromide 
• 25878-60-8 D-galactose pentaacetate 
• 3646-73-9 α-D-galactopyranose 
• 61-58-5 2-deoxy-D-lyxo-hexopyranose 
• 75828-75-0 1,3,4,6-Tetra-O-acetyl-2-desoxy-α/β-D-lyxo-hexopyranose 

Downstream Products

• 6605-29-4 methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 
• 55726-56-2 Acetic acid (2S,3S,6S)-6-acetoxymethyl-2-methoxy-3,6-dihydro-2H-pyran-3-yl ester 
• 6087-43-0 methyl 3,4,6-tri-O-acetyl-2-deoxy-β-D-lyxo-hexopyranoside 
• 6087-42-9 methyl 3,4,6-tri-O-acetyl-2-deoxy-α-D-galactoside 
• 86480-28-6 4'-fluoro-2'-(3,4,6-tri-O-acetyl-2-desoxy-α-D-threo-hex-2-enopyranosyl)anisole 
• 86388-93-4 4'-fluoro-3'-(3,4,6-tri-O-acetyl-2-desoxy-α-D-threo-hex-2-enopyranosyl)anisole 
• 88377-41-7 α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-threo-hex-2'-enopyranosyl)acetophenone 
• 88377-40-6 α-(4',6'-Di-O-acetyl-2',3'-dideoxy-β-D-threo-hex-2'-enopyranosyl)acetophenone 
• 122204-45-9 methyl 2,3,6-tri-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-talopyranosyl)-β-D-galactopyranoside 
• 86388-92-3 4'-nitro-2'-(3,4,6-tri-O-acetyl-2-desoxy-α-D-threo-hex-2-enopyranosyl)anisole 
• 150809-76-0 phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-D-galactopyranoside 
• 7226-42-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-fluoro-α-D-galactopyranose 
• 84278-00-2 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose 
• 108794-37-2 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-D-galactopyranoside 

Relevant academic research and scientific papers

Efficient and reproducible synthesis of an Fmoc-protected Tn antigen

This concise total synthesis of the Thomsen-Nouveau (Tn) glycoconjugate was accomplished using a palladium-catalyzed coupling between the glycosyl donor and Fmoc-protected serine acceptor. This is, to the best of our knowledge, the shortest synthesis reported from galactose for preparing this essential building block for large-scale solid phase peptide synthesis.

Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement

Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.

TARGETED PLASMA PROTEIN DEGRADATION

The present invention is directed to the bifunctional compounds and the use of such bifunctional compounds to lower plasma levels of extracellular target molecules by lysosomal degradation. Such bifunctional compounds have a cell surface receptor ligand covalently linked to a ligand that is capable of binding to an extracellular target molecule (such as a ligand for a growth factor, a cytokine, a chemokine, a hormone, a neurotransmitter, a capsid, a soluble receptor, an extracellular secreted protein, an antibody, a lipoprotein, an exosome, a virus, a cell, or a plasma membrane protein), where the cell surface receptor is associated with receptor mediated endocytosis, including asialoglycoprotein receptor (ASGPR) mediated lysosomal degradation and mannose-6-phosphate (M6PR) mediated lysosomal degradation. Pharmaceutical compositions comprising such bifunctional compounds and methods of treating a disease or disorder mediated by an extracellular molecule using such bifunctional compounds are also provided herein.

TARGETED BIFUNCTIONAL DEGRADERS

The present invention provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In another aspect, the present invention provides bifunctional compounds that can be used to promote or enhance degradation of certain autoantibodies. In certain embodiments, treatment or management of a disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein or the autoantibody in the subject. Thus, in certain embodiments, administration of a compound of the invention to the subject removes or reduces the circulation concentration of the circulating protein or the autoantibody, thus treating, ameliorating, or preventing the disease and/or disorder. In certain embodiments, the circulating protein is TNF.

ENGINEERED ANTIBODIES AS MOLECULAR DEGRADERS THROUGH CELLULAR RECEPTORS

The present disclosure provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In certain embodiments, the circulating protein mediates a disease and/or disorder in a subject, and treatment or management of the disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein in the subject. Thus, in certain embodiments, administration of a compound of the disclosure to the subject removes or reduces the circulation concentration of the circulating protein, thus treating, ameliorating, or preventing the disease and/or disorder.

Total Synthesis of Tri-, Hexa- and Heptasaccharidic Substructures of the O-Polysaccharide of Providencia rustigianii O34

A general and efficient strategy for synthesis of tri-, hexa- and heptasaccharidic substructures of the lipopolysaccharide of Providencia rustigianii O34 is described. For the heptasaccharide seven different building blocks were employed. Special features of the structures are an α-linked galactosamine and the two embedded α-fucose units, which are either branched at positions-3 and -4 or further linked at their 2-position. Convergent strategies focused on [4+3], [3+4], and [4+2+1] couplings. Whereas the [4+3] and [3+4] coupling strategies failed the [4+2+1] strategy was successful. As monosaccharidic building blocks trichloroacetimidates and phosphates were employed. Global deprotection of the fully protected structures was achieved by Birch reaction.

Positional Scanning MUC1 Glycopeptide Library Reveals the Importance of PDTR Epitope Glycosylation for Lectin Binding

One of the main barriers to explaining the functional significance of glycan-based changes in cancer is the natural epitope heterogeneity found on the surface of cancer cells. To help address this knowledge gap, we focused on designing synthetic tools to explore the role of tumor-associated glycans of MUC1 in the formation of metastasis via association with lectins. In this study, we have synthesized for the first time a MUC1-derived positional scanning synthetic glycopeptide combinatorial library (PS-SGCL) that vary in number and location of cancer-associated Tn antigen using the "tea bag" approach. The determination of the isokinetic ratios necessary for the equimolar incorporation of (glyco)amino acids mixtures to resin-bound amino acid was determined, along with developing an efficient protocol for on resin deprotection of O-acetyl groups. Enzyme-linked lectin assay was used to screen PS-SGCL against two plant lectins, Glycine max soybean agglutinin and Vicia villosa. The results revealed a carbohydrate density-dependent affinity trend and site-specific glycosylation requirements for high affinity binding to these lectins. Hence, PS-SGCLs provide a platform to systematically elucidate MUC1-lectin binding specificities, which in the long term may provide a rational design for novel inhibitors of MUC1-lectin interactions involved in tumor spread and glycopeptide-based cancer vaccines.

Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit

Zwitterionic polysaccharides (ZPSs) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β-(1 → 3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third-generation approach leverages a first in class glycosylation of a phosphoglycerol-functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.

Design and synthesis of trivalent Tn glycoconjugate polymers by nitroxide-mediated polymerization

A new synthetic method for preparing Tn glycoconjugate polymers, containing tumor-associated carbohydrate antigens, by controlled living radical polymerization is reported. To mimic the authentic structures of Tn glycopeptide antigens and to explore the controlled living radical polymerization, three tumor-associated carbohydrate antigens (GalNAc, GalNAcα1-O-Ser, and GalNAcα1-O-Thr) were attached to a styrene-type monomer through a diethylene glycol spacer. Under nitroxide-mediated polymerization, controlled living radical polymerization proceeded to afford defined glycopeptide polymers with different Tn densities and compositions. The polydispersity index (PDI) and molecular weights were increased and conversions were decreased upon increasing the concentration of Tn glycoconjugate monomers. The resulting Tn glycoconjugate polymers were characterized by NMR and IR. The spectral data indicate that the Tn glycoconjugate moiety did attach to the polymer chain and Tn glycoconjugate density could be adjusted through the nitroxide-mediated polymerization conditions. The number of Tn units containing in the polymer chains could be estimated by NMR integration. This synthetic approach provides a new and efficient tool for constructing novel Tn glycoconjugate polymers.

Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity

Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.