Tri-O-acetyl-D-glucal

Base Information

• Chemical Name: Tri-O-acetyl-D-glucal
• CAS No.: 2873-29-2
• Molecular Formula: C12H16O7
• Molecular Weight: 272.255
• Hs Code.: 29329995
• European Community (EC) Number: 220-709-0
• Nikkaji Number: J47.317K,J109.600A
• Mol file: 2873-29-2.mol

Synonyms:3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol;3,4,6-tri-O-acetyl-D-glucal;3,4,6-tri-O-acetylglucal

Chemical Property of Tri-O-acetyl-D-glucal

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 53-55 °C(lit.)
• Refractive Index: 1.484
• Boiling Point: 343.1 °C at 760 mmHg
• Flash Point: 149.2 °C
• PSA: 88.13000
• Density: 1.24 g/cm³
• LogP: 0.32540
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in chloroform and ethanol. Insoluble in water.
• 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%,≥99%, ^*data from raw suppliers

Tri-O-acetyl-D-glucal ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• 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
• Uses: A D-glucal derivative. 3,4,6-Tri-O-acetyl-D-glucal acts as a building block for the synthesis of oligosaccharides in both solution and solid-phase. Further, it is used in the preparation of D-arabino-1,5-anhydro-2-deoxy-hex-1-enitol.

Technology Process of Tri-O-acetyl-D-glucal

There total 122 articles about Tri-O-acetyl-D-glucal 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: 100.0%

D-Glucose (2280-44-6) + acetic anhydride (108-24-7) → D-glucal triacetate (2873-29-2)

Guidance literature:

D-Glucose; acetic anhydride; With hydrogen bromide; acetic anhydride; at 20 ℃;

With sodium acetate; copper(II) sulfate; acetic acid; zinc; In water; for 3.5h; Further stages.;

DOI:10.1021/ja069342g

Reference yield: 100.0%

Brigl's anhydride (3867-86-5,5624-44-2) → D-glucal triacetate (2873-29-2)

Guidance literature:

With dicyclohexylammonium salt of O,O-diethylphosphoroselenoic acid; In benzene; at 80 ℃; for 2h;

DOI:10.1016/S0040-4020(01)98912-4

Reference yield: 98.0%

acetobromomannose (13242-53-0) → D-glucal triacetate (2873-29-2)

Guidance literature:

With indium(III) chloride; indium; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; at 20 ℃; for 8h;

DOI:10.1021/jo0262964

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

3,4,6-tri-O-acetyl-D-glucal

lithium diphenylcuprate

1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose

Downstream raw materials:

D-glucal

D-lyxo-hexulose phenylosazone

C₁₅H₂₂HgO₁₀

C₁₅H₂₂HgO₁₀

Refernces

• 1、 Micskei, Károly,Juhász, Zsuzsa,Ratkovi?, Zoran R.,Somsák, László. "Reactivity of per-O-acetylated 1-thioglycosides and glycosyl sulfones towards chromium(II) complexes in aqueous medium". . p. 6117 - 6120. Retrieved 2006.
• 2、 Xu, Yun,Wang, Wenjun,Cai, Yu,Yang, Xia,Wang, Peng George,Zhao, Wei. "A convenient and efficient synthesis of glycals by zinc nanoparticles". . p. 46662 - 46665. Retrieved 2014.
• 3、 Gong, Hegui,Sinisi, Riccardo,Gagne, Michel R.. "A room temperature Negishi cross-coupling approach to C-alkyl glycosides". . p. 1908 - 1909. Retrieved 2007.
• 4、 Bhaumik, Atanu,Peterson, Gregory I.,Kang, Cheol,Choi, Tae-Lim. "Controlled Living Cascade Polymerization to Make Fully Degradable Sugar-Based Polymers from d -Glucose and d -Galactose". . p. 12207 - 12211. Retrieved 2019.
• 5、 Forbes,Franck. "Improved version of the Fischer-Zach synthesis of glycals: Vitamin B-12 catalyzed reductive elimination of glycosyl bromides". . p. 1424 - 1425. Retrieved 1999.
• 6、 -. "Method for efficiently constructing 1, 2-cis-2-nitro-glucoside and galactoside". Paragraph 0038; 0062. . Retrieved 2021/08/11.
• 7、 Ahmar, Mohammed,Li, Si-Zhe,Queneau, Yves,Soulère, Laurent,Zhang, Qiang. "Esters of Glucose-2-Phosphate: Occurrence and Chemistry". . . Retrieved 2020/07/02.