3,4,6-Tri-O-acetyl-D-galactal

Base Information

• Chemical Name: 3,4,6-Tri-O-acetyl-D-galactal
• CAS No.: 4098-06-0
• Molecular Formula: C12H16O7
• Molecular Weight: 272.255
• Hs Code.: 2932999099
• European Community (EC) Number: 223-859-5
• DSSTox Substance ID: DTXSID50193976
• Nikkaji Number: J1.102.931K,J224.904I
• Wikidata: Q63409465
• Mol file: 4098-06-0.mol

Synonyms:3,4,6-tri-O-acetyl-D-galactal

Chemical Property of 3,4,6-Tri-O-acetyl-D-galactal

Chemical Property:

• Appearance/Colour: pale yellow oil
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 34-38 °C(lit.)
• Refractive Index: 1.4645-1.4665
• Boiling Point: 343.1 °C at 760 mmHg
• Flash Point: 149.3 °C
• PSA: 88.13000
• Density: 1.24 g/cm³
• LogP: 0.32540
• Storage Temp.: Refrigerator (+4°C)
• Solubility.: Soluble in chloroform at 10mg/ml
• Water Solubility.: Insoluble
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 272.08960285
• Heavy Atom Count: 19
• Complexity: 388

Purity/Quality:

98% ^*data from raw suppliers

D-Galactal, Triacetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C=CO1)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@@H]([C@@H](C=CO1)OC(=O)C)OC(=O)C
• Chemical Composition and Structure: 3,4,6-Tri-O-acetyl-D-galactal is a monosaccharide consisting of three acetate groups, one galactose molecule, and one N-acetylglucosamine (GlcNAc) molecular composition. It usually appears as a white to off-white powder at room temperature.
• Uses: Biological Role:; 3,4,6-Tri-O-acetyl-D-galactal plays a crucial role in the synthesis of mucin glycoproteins, which are large, highly glycosylated molecules present on epithelial cell surfaces. These glycoproteins have diverse biological functions, including protection against pathogens and regulation of cell-cell interactions.; ; Synthesis of Oligosaccharides:; It serves as a building block for the synthesis of oligosaccharides, particularly 2,3-unsaturated glycopyranosides and 1,2-trans 3-amino-3-deoxyglycosides.; ; Industrial Applications:; It's derivatives are used as glycosyl donors in the synthesis of various oligosaccharides of bacterial, fungal, and mammalian origin.; ; Laboratory Methods:; It is utilized in chemical reactions such as the Ferrier rearrangement and aza-Wacker cyclization to synthesize structurally diverse glycosides.
• Production Methods: 3,4,6-Tri-O-acetyl-D-galactal can be synthesized by chemical or enzymatic methods. Chemical synthesis typically involves the modification of galactose molecules to introduce acetate groups at specific positions.
• General Description: 3,4,6-Tri-O-acetyl-D-galactal is a per-O-acetylated glycal derivative that serves as a key substrate in AuCl₃-catalyzed Ferrier reactions, enabling the synthesis of 2,3-unsaturated glycosides under mild conditions. Its activation by AuCl₃ facilitates reactions with diverse nucleophiles, including alcohols, thiols, and C-nucleophiles, while also offering potential for influencing β-anomer selectivity, which is typically difficult to achieve due to the anomeric effect. 3,4,6-Tri-O-acetyl-D-galactal's utility in glycosylation reactions highlights its importance in synthetic carbohydrate chemistry.

Technology Process of 3,4,6-Tri-O-acetyl-D-galactal

There total 52 articles about 3,4,6-Tri-O-acetyl-D-galactal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → triacetyl-D-galactal (4098-06-0)

Guidance literature:

With edetate disodium; chromium(II) acetate; In water; ethyl acetate; for 18h; Ambient temperature;

DOI:10.1016/0040-4039(95)02377-1

Reference yield: 98.0%

acetic anhydride (108-24-7) + D-galactal (21193-75-9) → triacetyl-D-galactal (4098-06-0)

Guidance literature:

With pyridine;

DOI:10.1021/acs.joc.9b02396

Reference yield: 94.0%

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(pyridine-2-sulfonyl)-tetrahydro-pyran-3-yl ester → triacetyl-D-galactal (4098-06-0)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(98)00568-1

upstream raw materials:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose

D-Galactose

2-pyridyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-D-lyxo-hexopyranoside

Downstream raw materials:

1,5-anhydro-3,4,6-tri-O-methyl-2-deoxy-D-lyxo-hex-1-enitol

1-(4',6'-di-O-acetyl-2',3'-dideoxy-α-D-threo-hex-2'-enopyranosyl)-2-phenylethyne

benzyl 2-((2R,3R)-3-hydroxy-tetrahydro-2H-pyran-2-yl)acetate

benzyl (2E)-3-[(2R,3R)-tetrahydro-3-hydroxy-2H-pyran-2-yl]-2-propenoate

Refernces

Scope of AuCl₃ in the activation of per-O-acetylglycals

10.1016/j.tet.2009.07.087

The research investigates the application of AuCl3 as a catalyst in the activation of per-O-acetylglycals and its subsequent use in the Ferrier reaction to produce 2,3-unsaturated glycosides. The study demonstrates that AuCl3 efficiently activates 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal, and 3,4-di-O-acetyl-L-rhamnal, enabling the Ferrier reaction with various nucleophiles at ambient conditions. The research also explores the potential of AuCl3 to influence the selectivity towards the formation of β-anomers, which are typically challenging to synthesize due to the anomeric effect. Key chemicals involved in the study include AuCl3 as the catalyst, per-O-acetylglycals such as 3,4,6-tri-O-acetyl-D-glucal, 3,4,6-tri-O-acetyl-D-galactal, and 3,4-di-O-acetyl-L-rhamnal as the substrates, and a range of nucleophiles like primary, secondary, allylic, benzylic, and propargylic alcohols, as well as thiol and C-nucleophiles. The study also examines the use of additives like AgSbF6, AgOTf, and LiClO4 in attempts to enhance the β-selectivity of the reactions.