[3,4-Diacetyloxy-5-(5-amino-4-carbamoylimidazol-1-yl)oxolan-2-yl]methyl acetate

Base Information

• Chemical Name: [3,4-Diacetyloxy-5-(5-amino-4-carbamoylimidazol-1-yl)oxolan-2-yl]methyl acetate
• CAS No.: 23274-21-7
• Molecular Formula: C15H20 N4 O8
• Molecular Weight: 384.346
• NSC Number: 157736
• DSSTox Substance ID: DTXSID10303291
• Mol file: 23274-21-7.mol

Synonyms:AICAR-Tri-O-Acetate;23274-21-7;[3,4-diacetyloxy-5-(5-amino-4-carbamoylimidazol-1-yl)oxolan-2-yl]methyl acetate;5-amino-1-(2,3,5-tri-o-acetylpentofuranosyl)-1h-imidazole-4-carboxamide;NSC157736;SCHEMBL14504924;DTXSID10303291;AKOS030254373;NSC-157736;5-Amino-1-(2',3',5'-tri-O-acetyl-beta-D-ribofuranosyl)-imidazole-4-carboxamide;FT-0662088;2-(acetoxymethyl)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)tetrahydrofuran-3,4-diyl diacetate

Chemical Property of [3,4-Diacetyloxy-5-(5-amino-4-carbamoylimidazol-1-yl)oxolan-2-yl]methyl acetate

Chemical Property:

• Vapor Pressure: 3.19E-15mmHg at 25°C
• Melting Point: 69 °C
• Boiling Point: 618.4°Cat760mmHg
• PKA: 15.28±0.50(Predicted)
• Flash Point: 327.8°C
• PSA: 175.06000
• Density: 1.61g/cm³
• LogP: 0.16960
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 384.12811361
• Heavy Atom Count: 27
• Complexity: 615

Purity/Quality:

97% ^*data from raw suppliers

5-Amino-1-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-imidazole-4-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(O1)N2C=NC(=C2N)C(=O)N)OC(=O)C)OC(=O)C

Technology Process of [3,4-Diacetyloxy-5-(5-amino-4-carbamoylimidazol-1-yl)oxolan-2-yl]methyl acetate

There total 2 articles about [3,4-Diacetyloxy-5-(5-amino-4-carbamoylimidazol-1-yl)oxolan-2-yl]methyl acetate 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: 95.0%

AICA riboside (2627-69-2) + acetic anhydride (108-24-7) → 5-Amino-4-carbamoyl-1β-(2',3',5'-tri-O-acetyl-D-ribofuranosyl)imidazole (23274-21-7)

Guidance literature:

With pyridine; at 20 ℃; for 15h;

DOI:10.3109/14756366.2015.1063622

Reference yield:

→ 5-Amino-4-carbamoyl-1β-(2',3',5'-tri-O-acetyl-D-ribofuranosyl)imidazole (23274-21-7)

Guidance literature:

Imidazol (I), Ac2O;

Reference yield: 93.0%

5-Amino-4-carbamoyl-1β-(2',3',5'-tri-O-acetyl-D-ribofuranosyl)imidazole (23274-21-7) → 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile (23192-63-4)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; for 2h; Ambient temperature;

DOI:10.1021/jm00106a045

upstream raw materials:

AICA riboside

acetic anhydride

Downstream raw materials:

5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile

2-formyladenosine

5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile

5-ethynyl-1-(β-D-ribofuranosyl)imidazole-4-carboxamide

Refernces

• 1、 -. "METHODS, COMPOSITIONS, AND FORMULATIONS FOR PREVENTING OR REDUCING ADVERSE EFFECTS IN A PATIENT". Page/Page column 25. . Retrieved 2008/12/07.
• 2、 -. "AICA riboside analogs". . . Retrieved 2008/06/13.