4098-06-0

Basic information

• Product Name: 3,4,6-Tri-O-acetyl-D-galactal
• Synonyms: (-)-TRI-O-ACETYL-D-GALACTAL;TRI-O-ACETYL-D-GALACTAL;D-GALACTAL TRIACETATE;3,4,6-TRI-O-ACETYL-D-GALACTAL;3,4,6-TRI-O-ACETYL-1,5-ANHYDRO-2-DEOXY-D-LYXO-HEX-1-ENITOL;3,4,6-TRI-O-ACETYL-1,5-ANHYDRO-D-LYXO-HEX-1-ENITOL;1,2-DIDEOXY-3,4,6-TRI-O-ACETYL-D-LYXO-1-HEXENOPYRANOSE;1,5-ANHYDRO-2-DEOXY-D-LYXO-HEX-1-ENITOL 3,4,6-TRI-O-ACETYL ETHER
• CAS NO: 4098-06-0
• Molecular Formula: C₁₂H₁₆O₇
• Molecular Weight: 272.25
• EINECS: 223-859-5
• Product Categories: Sugars, Carbohydrates & Glucosides;13C & 2H Sugars;Biochemistry;Galactose;Glycals;O-Substituted Sugars;Sugars;Carbohydrates & Derivatives
• Mol File: 4098-06-0.mol

Chemical Properties

• Melting Point: 34-38 °C(lit.)
• Boiling Point: 343.1 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: Pale Yellow/Oil or Solid
• Density: 1.24 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4645-1.4665
• Storage Temp.: Refrigerator (+4°C)
• Solubility: Soluble in chloroform at 10mg/ml
• Water Solubility: Insoluble
• CAS DataBase Reference: 3,4,6-Tri-O-acetyl-D-galactal(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-Tri-O-acetyl-D-galactal(4098-06-0)
• EPA Substance Registry System: 3,4,6-Tri-O-acetyl-D-galactal(4098-06-0)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 4098-06-0(Hazardous Substances Data)

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-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 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 
• 108-24-7 acetic anhydride 
• 21193-75-9 D-galactal 
• 14227-54-4 2,3,4,6-tetra-O-acetyl-α-D-talopyranosyl bromide 
• 10257-28-0 D-Galactose 
• 25878-60-8 D-galactose pentaacetate 
• 14227-87-3 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl chloride 
• 75-36-5 acetyl chloride 
• 75-65-0 tert-butyl alcohol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 66966-07-2 α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate 

Downstream Products

• 201053-37-4 (-)-3,6-O-bis(triisopropylsilyl)-D-galactal 
• 221662-13-1 methyl 2-deoxy-4,6-O-benzylidene-α-D-galactopyranoside 
• 124579-80-2 1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-lyxo-hex-1-enitol 
• 69247-21-8 2'-iodobenzyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-eno-pyranoside 
• 19940-05-7 6-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 150809-76-0 phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-seleno-α-D-galactopyranoside 
• 16740-98-0 1,5-anhydro-3,4,6-tri-O-methyl-2-deoxy-D-lyxo-hex-1-enitol 
• 879906-21-5 1-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-threo-hex-2'-enopyranosyl)-2-phenylethyne 
• 96093-11-7 Methyl-2-azido-4,6-O-benzylidene-2-desoxy-β-D-galactopyranoside 

Relevant articles and documents

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.

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.

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.

Method for stereoselectively synthesizing beta-2-deoxyglycoside bond

The invention discloses a method for stereoselectively synthesizing a beta-2-deoxyglycoside bond. The method comprises the following steps: performing glycosylation on 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene serving as a donor, a saccharide receptor and a molecular sieve under the condition of the existence of an accelerant, wherein an isopropyl acetal protectivegroup is mounted on a 3-site hydroxyl and a 4-site hydroxyl of the 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene and a TBDPS is mounted on the 6-site of the 3,4-O-isopropylidene-6-O-tert-butyl diphenylmethyl silicone-D-galactosene; through the synergistic effect of the protective groups, sugar ring conformation of the donor is controlled, and the stereoselective synthesis of a beta-configuration is realized. According to the method, the stereoselectivity of the glycosylation can be controlled effectively and stereoselectively; the method is wide in substrate application range and convenient to operate; raw materials are easy to obtain; side reactions of the glycosylation are few; a target product is high in yield and optical purity; a new design thought is provided for the research of the glycosylation.

Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals

A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.

Synthesis and conformational preferences of short analogues of antifreeze glycopeptides (AFGP)

Antifreeze glycoproteins are a class of biological agents which enable living at temperatures below the freezing point of the body fluids. Antifreeze glycopeptides usually consist of repeating tripeptide unit (-Ala-Ala-Thr?-), glycosylated at the threonine side chain. However, on the microscopic level, the mechanism of action of these compounds remains unclear. As previous research has shown, antifreeze activity of antifreeze glycopeptides strongly relies on the overall conformation of the molecule as well an on the stereochemistry of amino acid residues. The desired monoglycosylated analogues with acetylated amino termini and the carboxy termini in form of N-methylamide have been synthesized. Conformational nuclear magnetic resonance (NMR) studies of the designed analogues have shown a strong influence of the stereochemistry of amino acid residues on the peptide chain stability, which could be connected to the antifreeze activity of these compounds. A better understanding of the mechanism of action of antifreeze glycopeptides would allow applying these materials, e.g., in food industry and biomedicine.