Isomugineic acid

Base Information

• Chemical Name: Isomugineic acid
• CAS No.: 69199-37-7
• Molecular Formula: C12H20 N2 O8
• Molecular Weight: 320.299
• DSSTox Substance ID: DTXSID90988904
• Nikkaji Number: J3.246.272C
• Wikipedia: Mugineic_acid
• Wikidata: Q3604542
• Mol file: 69199-37-7.mol

Synonyms:Isomugineic acid;Mugineic_acid;SCHEMBL13131755;DTXSID90988904;CHEBI:175088;Q3604542;4-[3-(2-Carboxyazetidine-1-yl)-1-carboxy-2-hydroxypropylamino]-2-hydroxybutanoic acid;1-[3-carboxy-3-[(3-carboxy-3-hydroxypropyl)amino]-2-hydroxypropyl]azetidine-2-carboxylic acid;N-[3-((3-carboxy-3-hydroxypropyl)amino)-3-carboxy-2-hydroxypropyl] azetidine-2-carboxylic acid

Chemical Property of Isomugineic acid

Chemical Property:

• Vapor Pressure: 1.4E-23mmHg at 25°C
• Boiling Point: 714.4°C at 760 mmHg
• Flash Point: 385.9°C
• PSA: 167.63000
• Density: 1.561g/cm³
• LogP: -2.28660
• XLogP3: -6.7
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 320.12196560
• Heavy Atom Count: 22
• Complexity: 429

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(C1C(=O)O)CC(C(C(=O)O)NCCC(C(=O)O)O)O

Technology Process of Isomugineic acid

There total 6 articles about Isomugineic 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: 92.0%

tert-butyl (2S,2'S,3'S,3''S)-3'-(3''-tert-butoxycarbonyl-3''-tert-butyldimethylsilyloxypropylamino)-3'-tert-butoxycarbonyl-2'-methoxymethyloxypropyl-2-azetidinecarboxylate (146565-68-6) → mugineic acid (69199-37-7)

Guidance literature:

With hydrogenchloride; methoxybenzene; In tetrahydrofuran; for 40h; Heating;

DOI:10.1016/S0040-4039(00)74778-2

Reference yield: 71.0%

(S)-1-[(2S,3S)-3-Benzyloxycarbonyl-3-((R)-3-benzyloxycarbonyl-3-benzyloxymethoxy-propylamino)-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-azetidine-2-carboxylic acid benzyl ester (105762-98-9) → mugineic acid (69199-37-7)

Guidance literature:

With methanesulfonic acid; methoxybenzene; for 4h; Ambient temperature;

DOI:10.1021/jo00376a102

Reference yield:

C24H44N2O8 (1028191-78-7) → 2'-epi-mugineic acid (958350-33-9) + mugineic acid (69199-37-7)

Guidance literature:

With hydrogenchloride; water; at 20 ℃; for 5h; Resolution of diastereomers;

upstream raw materials:

tert-butyl (2S,2'S,3'S,3''S)-3'-(3''-tert-butoxycarbonyl-3''-tert-butyldimethylsilyloxypropylamino)-3'-tert-butoxycarbonyl-2'-methoxymethyloxypropyl-2-azetidinecarboxylate

(S)-1-[(2S,3S)-3-Benzyloxycarbonyl-3-((R)-3-benzyloxycarbonyl-3-benzyloxymethoxy-propylamino)-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-azetidine-2-carboxylic acid benzyl ester

C₂₄H₄₄N₂O₈

Refernces

• 1、 Namba, Kosuke,Murata, Yoshiko,Horikawa, Manabu,Iwashita, Takashi,Kusumoto, Shoichi. "A practical synthesis of the phytosiderophore 2′-deoxymugineic acid: A key to the mechanistic study of iron acquisition by graminaceous plants". . p. 7060 - 7063. Retrieved 2008/09/18.
• 2、 Matsuura, Fumiyoshi,Hamada, Yasumasa,Shioiri, Takayuki. "Efficient Synthesis of Mugineic Acid, A Typical Phytosiderophore, Utilizing the Phenyl Group as the Carboxyl Synthon". . p. 7917 - 7920. Retrieved 2007/10/02.