[5-(2-Amino-5-isobutyl-1,3-thiazol-4-yl)-2-furyl]phosphonic acid

Base Information

• Chemical Name: [5-(2-Amino-5-isobutyl-1,3-thiazol-4-yl)-2-furyl]phosphonic acid
• CAS No.: 261365-11-1
• Molecular Formula: C11H15N2O4PS
• Molecular Weight: 302.28700
• UNII: 9379MH4CAL
• ChEMBL ID: CHEMBL495498
• Nikkaji Number: J2.209.818G
• Pharos Ligand ID: UABT181UDGHL
• Mol file: 261365-11-1.mol

Synonyms:(5-(2-amino-5-(2-methylpropyl)-4-thiazolyl)-2-furanyl)phosphonic acid;MB 05032;MB-05032;MB05032

Chemical Property of [5-(2-Amino-5-isobutyl-1,3-thiazol-4-yl)-2-furyl]phosphonic acid

Chemical Property:

• Boiling Point: 576.7±60.0 °C(Predicted)
• PKA: 0.98±0.10(Predicted)
• PSA: 147.63000
• Density: 1.47±0.1 g/cm3(Predicted)
• LogP: 2.56800
• Solubility.: Soluble in DMSO
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 302.04901514
• Heavy Atom Count: 19
• Complexity: 365

Purity/Quality:

>98% ^*data from raw suppliers

MB05032 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1=C(N=C(S1)N)C2=CC=C(O2)P(=O)(O)O

Technology Process of [5-(2-Amino-5-isobutyl-1,3-thiazol-4-yl)-2-furyl]phosphonic acid

There total 5 articles about [5-(2-Amino-5-isobutyl-1,3-thiazol-4-yl)-2-furyl]phosphonic acid 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%

2-amino-5-isobutyl-4-[2-(5-diethylphosphono)furanyl]thiazole (261372-76-3) → MB 05032 (261365-11-1)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ja074871l

Reference yield:

[5-(4-methylpentanoyl)furan-2-yl]phosphonic acid diethyl ester (213125-12-3) → MB 05032 (261365-11-1)

Guidance literature:

Multi-step reaction with 3 steps

1: copper(ll) bromide / ethyl acetate; chloroform / 24 h / 20 °C

2: ethanol / 2 h / Reflux

3: trimethylsilyl bromide / dichloromethane / 16 h / 20 °C / Inert atmosphere

With trimethylsilyl bromide; copper(ll) bromide; In ethanol; dichloromethane; chloroform; ethyl acetate;

Reference yield:

[5-(2-bromo-4-methylpentanoyl)furan-2-yl]phosphonic acid diethyl ester (347869-08-3) → MB 05032 (261365-11-1)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 2 h / Reflux

2: trimethylsilyl bromide / dichloromethane / 16 h / 20 °C / Inert atmosphere

With trimethylsilyl bromide; In ethanol; dichloromethane;

upstream raw materials:

2-amino-5-isobutyl-4-[2-(5-diethylphosphono)furanyl]thiazole

[5-(4-methylpentanoyl)furan-2-yl]phosphonic acid diethyl ester

[5-(2-bromo-4-methylpentanoyl)furan-2-yl]phosphonic acid diethyl ester

4-Methylpentanoic acid

Downstream raw materials:

2-amino-4-[2-(5-(O-phenyl)-(N-((S)-1-ethoxycarbonyl)ethyl)phosphonamido)furanyl]-5-isobutylthiazole hydrochloride

Refernces

• 1、 Dang, Qun,Kasibhatla, Srinivas Rao,Reddy, K. Raja,Jiang, Tao,Reddy, M. Rami,Potter, Scott C.,Fujitaki, James M.,Van Poelje, Paul D.,Huang, Jingwei,Lipscomb, William N.,Erion, Mark D.. "Discovery of potent and specific fructose-1,6-bisphosphatase inhibitors and a series of orally-bioavailable phosphoramidase-sensitive prodrugs for the treatment of type 2 diabetes". . p. 15491 - 15502. Retrieved 2008/09/19.