alpha-D-Glucose pentaacetate

Base Information

• Chemical Name: alpha-D-Glucose pentaacetate
• CAS No.: 604-68-2
• Molecular Formula: C16H22O11
• Molecular Weight: 390.344
• Hs Code.: 29400000
• European Community (EC) Number: 210-073-2
• UNII: 1CS424NS93
• DSSTox Substance ID: DTXSID10883462
• Nikkaji Number: J6.815B
• Wikidata: Q27252242
• ChEMBL ID: CHEMBL378840
• Mol file: 604-68-2.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 alpha-D-Glucose pentaacetate

Chemical Property:

• Appearance/Colour: odorless white powder
• Vapor Pressure: 0-0Pa at 20-50℃
• Melting Point: 111-113 °C
• Refractive Index: 105.5 ° (C=1.5, MeOH)
• 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.: Sealed in dry,Room Temperature
• Solubility.: chloroform: 0.1 g/mL, clear, colorless
• Water Solubility.: < 5 G/L (25℃)
• 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

1,2,3,4,6-Penta-O-acetyl-a-D-glucopyranose ^*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:

• 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: D-Glucose pentaacetate was reported to stimulate insulin release in rat pancreatic islets. Only α-D-glucose pentaacetate caused an immediate increase in insulin output. The β-anomer of D-glucose pentaacetate first transiently inhibited insulin release, this initial effect being followed by a secondary rise in secretory rate.

Technology Process of alpha-D-Glucose pentaacetate

There total 79 articles about alpha-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:

β-D-glucose pentaacetate (604-69-3) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) + α-D-glucopyranose peracetylate (604-68-2)

Guidance literature:

With bromine; In ethyl acetate; at 20 ℃; for 19h; Irradiation; Darkness; Green chemistry;

DOI:10.1016/j.tetlet.2013.10.088

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:

1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside

S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside

1-O-phenyl-2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside

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、 Li, Xiao-San,Chen, Tang-Ji,Xu, Zhi-Peng,Long, Juan,He, Miao-Ying,Zhan, He-Hui,Zhuang, Hai-Cai,Wang, Qi-Lin,Liu, Li,Yang, Xue-Mei,Tang, Jin-Shan. "Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents". . . Retrieved 2021/12/30.