Phosphoramidon

Base Information

• Chemical Name: Phosphoramidon
• CAS No.: 36357-77-4
• Molecular Formula: C23H34N3O10P
• Molecular Weight: 543.511
• European Community (EC) Number: 252-996-3
• UNII: T3G94E2LB1
• DSSTox Substance ID: DTXSID601317292
• Nikkaji Number: J18.388A
• Wikipedia: Phosphoramidon
• Wikidata: Q7187544
• Pharos Ligand ID: XR9AFC9QP1RG
• Metabolomics Workbench ID: 69920
• ChEMBL ID: CHEMBL479579
• Mol file: 36357-77-4.mol

Synonyms:2-((2-((hydroxy((3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)phosphoryl)amino)-4-methylpentanoyl)amino)-3-(1H-indol-3-yl)propionate disodium salt;N-(alpha-L-rhamnopyranosyloxyhydroxyphosphinyl)-L- leucyl-L-tryptophan;phosphoramidon

Chemical Property of Phosphoramidon

Chemical Property:

• PKA: -0.66±0.50(Predicted)
• PSA: 220.48000
• Density: 1.48 g/cm³
• LogP: 1.01040
• Storage Temp.: −20°C
• Solubility.: H2O: 1 mM Stock solution stable for 1 month at –20&#
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 543.19818129
• Heavy Atom Count: 37
• Complexity: 848

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OP(=O)(NC(CC(C)C)C(=O)NC(CC2=CNC3=CC=CC=C32)C(=O)O)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OP(=O)(N[C@@H](CC(C)C)C(=O)N[C@@H](CC2=CNC3=CC=CC=C32)C(=O)O)O)O)O)O

Technology Process of Phosphoramidon

There total 2 articles about Phosphoramidon 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: 15.0%

(S)-3-(1H-Indol-3-yl)-2-{(S)-4-methyl-2-[phenoxy-((3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-phosphorylamino]-pentanoylamino}-propionic acid ethyl ester → phosphoramidon (36357-77-4) + phosphoramidon

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 48h; Ambient temperature;

DOI:10.1016/0040-4039(95)00024-7

Reference yield:

N-Phospho-L-leucyl-L-tryptophan (56361-75-2) + thymidine 5'-diphospho-β-L-rhamnose (2147-59-3,62012-79-7) → phosphoramidon (36357-77-4)

Guidance literature:

With glycosyltransferase TalC; at 30 ℃; for 16h; Catalytic behavior; Enzymatic reaction;

DOI:10.1039/c9sc00641a

Reference yield:

Talopeptin (36357-77-4,79733-80-5,84235-60-9,121570-15-8) → 6-Deoxy-L-talose (7658-10-8,478518-52-4) + L-leucyl-L-tryptophan (5156-22-9)

Guidance literature:

With hydrogenchloride;

DOI:10.1016/S0040-4039(00)87331-1

upstream raw materials:

N-Phospho-L-leucyl-L-tryptophan

thymidine 5'-diphospho-β-L-rhamnose

Downstream raw materials:

6-Deoxy-L-talose

L-leucyl-L-tryptophan

Refernces

• 1、 De Nanteuil, Guillaume,Benoist, Alain,Remond, Georges,Descombes, Jean-Jacques,Barou, Veronique,Verbeuren, Tony J.. "Synthesis of the endothelin converting enzyme inhibitor phosphoramidon". . p. 1435 - 1438. Retrieved 2007/10/02.