Fosmidomycin

Base Information

• Chemical Name: Fosmidomycin
• CAS No.: 66508-53-0
• Molecular Formula: C4H9NNaO5P
• Molecular Weight: 183.10
• Hs Code.: 2931900090
• UNII: 5829E3D9I9
• DSSTox Substance ID: DTXSID70216712
• Nikkaji Number: J431.386K
• Wikipedia: Fosmidomycin
• Wikidata: Q905038
• NCI Thesaurus Code: C65764
• Metabolomics Workbench ID: 52755
• ChEMBL ID: CHEMBL203125
• Mol file: 66508-53-0.mol

Synonyms:3-(N-formyl-N-hydroxy)aminopropylphosphonic acid;fosfidomycin;fosmidomycin;fosmidomycin monoammonium salt;fosmidomycin monopotassium salt;fosmidomycin monosodium salt;fosmidomycin sodium;fosmidomycin sodium salt;FR-31564;phosphonic acid, (3-(formylhydroxyamino)propyl)-, monosodium salt

Chemical Property of Fosmidomycin

Chemical Property:

• Vapor Pressure: 6.94E-10mmHg at 25°C
• Melting Point: 158-160° (dec); mp 160-166° (dec) (Hemmi)
• Refractive Index: 1.533
• Boiling Point: 463.7±55.0 °C at 760 mmHg
• Flash Point: 234.3±31.5 °C
• PSA: 107.88000
• Density: 1.6±0.1 g/cm³
• LogP: 0.03770
• Storage Temp.: ?20°C
• Solubility.: H2O: soluble20mg/mL, clear
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 183.02965942
• Heavy Atom Count: 11
• Complexity: 166

Purity/Quality:

99% ^*data from raw suppliers

Fosmidomycin sodium salt hydrate ≥95% (NMR) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CN(C=O)O)CP(=O)(O)O
• Recent ClinicalTrials: Fosmidomycin and Azithromycin for Acute Uncomplicated Plasmodium Falciparum Malaria (P. Malaria) in Adults
• Uses: Fosmidomycin sodium salt hydrate has been used as an inhibitor of 1-deoxy-D-xylulose 5-phosphate reductoisomerase in a study to determine monotropin carvacrol biosynthesis in Satureja khuzistanica plant.

Technology Process of Fosmidomycin

There total 4 articles about Fosmidomycin 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: 89.0%

diethyl 3-(N-formyl-N-hydroxyamino)propylphosphonate (66508-68-7) → fosmidomycin (66508-53-0)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2012.11.049

Reference yield: 70.0%

3-(N-hydroxyamino)-propylphosphonic acid (66508-11-0) + formyl acetic anhydride (2258-42-6) → fosmidomycin (66508-53-0)

Guidance literature:

for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)93633-5

Reference yield:

Arg (7200-25-1,25212-18-4) + 3-(N-hydroxyamino)-propylphosphonic acid (66508-11-0) → fosmidomycin (66508-53-0)

Guidance literature:

With formic acid; acetic anhydride; In water;

upstream raw materials:

formic acid

3-(N-hydroxyamino)-propylphosphonic acid

formyl acetic anhydride

Arg

Downstream raw materials:

fosmidomycin mono sodium salt

Refernces

• 1、 Suresh, Surisetti,Shyamraj, Dharavath,Larhed, Mats. "Synthesis of antimalarial compounds fosmidomycin and FR900098 through N- or P-alkylation reactions". . p. 1183 - 1188. Retrieved 2013/03/14.
• 2、 Kamiya, Takashi,Hemmi, Keiji,Takeno, Hidekazu,Hashimoto, Masashi. "STUDIES ON PHOSPHONIC ACID ANTIBIOTICS. I. STRUCTURE AND SYNTHESIS OF 3-(N-ACETYL-N-HYDROXYAMINO)PROPYLPHOSPHONIC ACID (FR-900098) AND ITS N-FORMYL ANALOGUE (FR-31564)". . p. 95 - 98. Retrieved 2007/10/02.