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.

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:

Acetic acid (2R,3R,6R)-2-acetoxymethyl-6-methoxy-3,6-dihydro-2H-pyran-3-yl ester

Acetic acid (2R,3R,6S)-2-acetoxymethyl-6-methoxy-3,6-dihydro-2H-pyran-3-yl ester

Acetic acid (2S,3R,6S)-2-acetoxymethyl-6-methoxy-3,6-dihydro-2H-pyran-3-yl ester

Acetic acid (2S,3R,6R)-2-acetoxymethyl-6-methoxy-3,6-dihydro-2H-pyran-3-yl ester

Refernces

• 1、 -. "TARGETED BIFUNCTIONAL DEGRADERS". Page/Page column 157. . Retrieved 2021/04/17.
• 2、 -. "TARGETED PLASMA PROTEIN DEGRADATION". Page/Page column 172; 175-176. . Retrieved 2021/08/14.