2'-Deoxymugineic acid

Base Information

• Chemical Name: 2'-Deoxymugineic acid
• CAS No.: 74235-24-8
• Molecular Formula: C₁₂H₂₀N₂O₇
• Molecular Weight: 304.3
• DSSTox Substance ID: DTXSID50995715
• Wikidata: Q27109156
• Metabolomics Workbench ID: 53681
• Mol file: 74235-24-8.mol

Synonyms:(13C4)-2'-deoxymugineic acid;2'-deoxymugineic acid;2'-DMA

Chemical Property of 2'-Deoxymugineic acid

Chemical Property:

• Vapor Pressure: 8.02E-20mmHg at 25°C
• Boiling Point: 653.1°C at 760 mmHg
• PKA: 2.07±0.10(Predicted)
• Flash Point: 348.8°C
• PSA: 147.40000
• Density: 1.468g/cm³
• LogP: -1.25740
• XLogP3: -5.7
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 304.12705098
• Heavy Atom Count: 21
• Complexity: 401

Purity/Quality:

99%min ^*data from raw suppliers

2’-DeoxymugineicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(C1C(=O)O)CCC(C(=O)O)NCCC(C(=O)O)O
• Isomeric SMILES: C1CN([C@@H]1C(=O)O)CC[C@@H](C(=O)O)NCC[C@@H](C(=O)O)O
• Uses: Phytosiderophores are produced in higher plants as iron chelating amino acids that promote uptake of iron from soil

Technology Process of 2'-Deoxymugineic acid

There total 45 articles about 2'-Deoxymugineic 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: 100.0%

(S)-1-[(S)-3-Benzyloxycarbonyl-3-((S)-3-benzyloxycarbonyl-3-hydroxy-propylamino)-propyl]-azetidine-2-carboxylic acid (848785-47-7) → 2'-deoxymugineic acid (74235-24-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 3102.89 Torr;

DOI:10.1016/j.tetlet.2005.01.030

Reference yield: 95.0%

(S)-1-((S)-4-(tert-butoxy)-3-((tert-butoxycarbonyl)((S)-3,4-di-tert-butoxy-4-oxobutyl)amino)-4-oxobutyl)azetidine-2-carboxylic acid → 2'-deoxymugineic acid (74235-24-8)

Guidance literature:

With hydrogenchloride; methoxybenzene; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

DOI:10.1002/chem.202004004

Reference yield: 93.0%

(2S,3S,3''S)-N-[3-(3-acetoxy-3-methoxycarbonylpropylamino)-3-t-butoxycarbonylpropyl]azetidine-2-carboxylic acid t-butyl ester (344299-89-4) → 2'-deoxymugineic acid (74235-24-8)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 3h;

DOI:10.1016/S0040-4020(01)00215-0

upstream raw materials:

(S)-1-[(S)-3-((S)-3-Acetoxy-3-ethoxycarbonyl-propylamino)-3-ethoxycarbonyl-propyl]-azetidine-2-carboxylic acid methyl ester

(S)-1-((S)-3-Benzyloxycarbonyl-3-{[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-tert-butoxycarbonyl-amino}-propyl)-azetidine-2-carboxylic acid benzyl ester

tert-butyl (2S,3'S,3S)-3'-(3-acetoxy-N-tert-butoxycarbonyl-3-tert-butoxycarbonylpropylamino)-3'-tert-butoxycarbonylpropyl-2-azetidinecarboxylate

(S)-1-{(S)-3-tert-Butoxycarbonyl-3-[(S)-3-tert-butoxycarbonyl-3-(tert-butyl-dimethyl-silanyloxy)-propylamino]-propyl}-azetidine-2-carboxylic acid tert-butyl ester

Refernces

• 1、 -. "EFFECTIVE PRODUCTION PROCESS FOR MUGINEIC ACID COMPOUND". Page/Page column 13. . Retrieved 2009/10/01.
• 2、 Singh, Satendra,Crossley, George,Ghosal, Saswati,Lefievre, Yann,Pennington, Michael W.. "A short practical synthesis of 2′-deoxymugineic acid". . p. 1419 - 1421. Retrieved 2007/10/03.