beta-D-Glucose pentaacetate

Base Information

• Chemical Name: beta-D-Glucose pentaacetate
• CAS No.: 604-69-3
• Molecular Formula: C16H22O11
• Molecular Weight: 390.344
• Hs Code.: 29400090
• European Community (EC) Number: 210-074-8
• UNII: V833P95COC
• Nikkaji Number: J14.175E
• Wikidata: Q27291653
• ChEMBL ID: CHEMBL438446
• Mol file: 604-69-3.mol

Synonyms:1,2,3,4,6-penta-O-acetyl-alpha-D-glucopyranoside;beta-D-glucose pentaacetate;glucose pentaacetate;glucose pentaacetate, (alpha-D)-isomer;glucose pentaacetate, (beta-(D))-isomer;glucose pentaacetate, (D)-isomer;penta-O-acetyl-alpha-D-glucopyranose;penta-O-acetylglucopyranose

Chemical Property of beta-D-Glucose pentaacetate

Chemical Property:

• Appearance/Colour: white to beige powder
• Vapor Pressure: 9.23E-08mmHg at 25°C
• Melting Point: 130-132 °C
• Refractive Index: 4.5 ° (C=5, CHCl3)
• Boiling Point: 434.8 °C at 760 mmHg
• Flash Point: 188.1 °C
• PSA: 140.73000
• Density: 1.3 g/cm³
• LogP: -0.36740
• Storage Temp.: 2-8°C
• Solubility.: chloroform: 0.1 g/mL, clear, colorless
• Water Solubility.: Soluble in chloroform and methanol. Insoluble in water.
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 390.11621151
• Heavy Atom Count: 27
• Complexity: 599

Purity/Quality:

99%, ^*data from raw suppliers

b-D-Glucose Pentaacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 21-36/38-46-62-63
• Safety Statements: 24/25-53-36/37-26-25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: beta-D-Glucose pentaacetate was reported to stimulate insulin release in rat pancreatic islets. β-D-Glucose Pentaacetate is used in biochemical reaction and also used as an active pharmaceutical intermediate. Further, it is used to stimulate insulin release in rat pancreatic islets.

Technology Process of beta-D-Glucose pentaacetate

There total 75 articles about beta-D-Glucose pentaacetate 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:

D-Glucose (2280-44-6) + acetic anhydride (108-24-7) → Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester (604-70-6) + β-D-glucose pentaacetate (604-69-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1002/chem.201103028

Reference yield:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-[(4-methoxyphenyl)thio]tetrahydro-2H-pyran-3,4,5-triyl triacetate (85951-15-1) → methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4860-85-9) + Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester (604-70-6) + β-D-glucose pentaacetate (604-69-3) + α-D-glucopyranose peracetylate (604-68-2)

Guidance literature:

In methanol; acetonitrile; Yield given. Yields of byproduct given. Title compound not separated from byproducts; electrochemical synthesis: one compartment, three-electrode, air-tight cell, vitrous carbon anode and Pt catode, 0.2 M LiClO₄ as supporting electrolyte, constant potential 1.34 V (vs standard calomel reference electrode);

Reference yield:

2',4',6'-Trimethoxyphenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (172847-87-9) → methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (4860-85-9) + Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester (604-70-6) + β-D-glucose pentaacetate (604-69-3) + α-D-glucopyranose peracetylate (604-68-2)

Guidance literature:

In methanol; acetonitrile; Yield given. Yields of byproduct given. Title compound not separated from byproducts; electrochemical synthesis: one compartment, three-electrode, air-tight cell, vitrous carbon anode and Pt catode, 0.2 M LiClO₄ as supporting electrolyte, constant potential 1.20 V (vs standard calomel reference electrode);

upstream raw materials:

β-D-mannose

acetic anhydride

D-Mannose

D-Mannose

Downstream raw materials:

homoarbutin

(2,4,6-triiodo-phenyl)-(tetra-O-acetyl-α-D-glucopyranoside)

(2,4,6-triiodo-phenyl)-(tetra-O-acetyl-β-D-glucopyranoside)

4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylbenzoate

Refernces

• 1、 Ahmed, Ajaz,Bhagat, Kavita,Choudhary, Sushil,Kaur Gulati, Harmandeep,Kumar, Ajay,Kumar, Nitish,Mukherjee, Debaraj,Singh Bedi, Preet Mohinder,Singh, Atamjit,Singh, Harbinder,Vir Singh, Jatinder. "Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity". . . Retrieved 2021/11/23.
• 2、 ?ezanka, Michal,Dolensky, Bohumil,Krabicová, Ilona. "Selectivity of 1-O-Propargyl-D-Mannose Preparations". . . Retrieved 2022/03/01.