Nittp

Base Information

• Chemical Name: Nittp
• CAS No.: 150196-34-2
• Molecular Formula: C18H23 N3 O7 S
• Molecular Weight: 425.46
• UNII: A99BB7VWS4
• Nikkaji Number: J1.102.318E
• Mol file: 150196-34-2.mol

Synonyms:NITTP;150196-34-2;Fmiso precursor;A99BB7VWS4;[3-(2-nitroimidazol-1-yl)-2-(oxan-2-yloxy)propyl] 4-methylbenzenesulfonate;3-(2-Nitro-1H-imidazol-1-yl)-2-((tetrahydro-2H-pyran-2-yl)oxy)propyl 4-methylbenzenesulfonate;1-(2/'-NITRO-1/'-IMIDAZOLYL)-2-O-TETRAHYDROPYRANYL-3-O-TOLUENESULFONYL-PROPANEDIOL;UNII-A99BB7VWS4;SCHEMBL13020449

Chemical Property of Nittp

Chemical Property:

• Melting Point: 105-107 °C
• Boiling Point: 659.1±65.0 °C(Predicted)
• PKA: 0.78±0.33(Predicted)
• PSA: 133.85000
• Density: 1.43±0.1 g/cm3(Predicted)
• LogP: 4.02100
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 8
• Exact Mass: 425.12567125
• Heavy Atom Count: 29
• Complexity: 628

Purity/Quality:

1-(2'-NITRO-1'-IMIDAZOLYL)-2-O-TETRAHYDROPYRANYL-3-O-TOLUENESULFONYL-PROPANEDIOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC(CN2C=CN=C2[N+](=O)[O-])OC3CCCCO3
• Recent EU Clinical Trials: Ensayo fase I/II de escalada de dosis de radioterapia sobre regiones hipóxicas determinadas con F18-fluoromisonidazol (FMISO)-PET/TC en cáncer de pulmón.

Technology Process of Nittp

There total 6 articles about Nittp 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: 88.0%

3,4-dihydro-2H-pyran (110-87-2) + toluene-4-sulfonic acid 2-hydroxy-3-(2-nitroimidazol-1-yl)propyl ester (378230-70-7) → 1-(2′-nitro-1′-imidazolyl)-2-O-tetrahydropyranyl-3-O-toluenesulfonyl-propanediol (150196-34-2)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 7h; optical yield given as %de;

DOI:10.1055/s-0030-1258269

Reference yield: 40.0%

2-((tetrahydro-2H-pyran-2-yl)oxy)propane-1,3-diyl bis(4-methylbenzenesulfonate) (150196-32-0) + 2-nitro-1H-imidazole (527-73-1) → 1-(2′-nitro-1′-imidazolyl)-2-O-tetrahydropyranyl-3-O-toluenesulfonyl-propanediol (150196-34-2)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide;

DOI:10.1002/jlcr.1001

Reference yield:

2-(tetrahydro-2H-pyran-2-yloxy)propane-1,3-diol (150196-31-9) → 1-(2′-nitro-1′-imidazolyl)-2-O-tetrahydropyranyl-3-O-toluenesulfonyl-propanediol (150196-34-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 6.1 g / pyridine

2: 40 percent / Cs₂CO₃ / dimethylformamide

With pyridine; caesium carbonate; In N,N-dimethyl-formamide;

DOI:10.1002/jlcr.1001

upstream raw materials:

2-((tetrahydro-2H-pyran-2-yl)oxy)propane-1,3-diyl bis(4-methylbenzenesulfonate)

2-nitro-1H-imidazole

2-(tetrahydro-2H-pyran-2-yloxy)propane-1,3-diol

2-(tetrahydro-2H-pyran-2-yloxy)propane-1,3-diyl diacetate

Downstream raw materials:

Fluoromisonidazole

Refernces

• 1、 Nieto, Elena,Alajarin, Ramon,Alvarez-Builla, Julio,Larranaga, Ignacio,Gorospe, Elena,Pozo, Miguel A.. "A new and improved synthesis of the precursor of the hypoxia marker [ 18F]-FMISO". experimental part. p. 3700 - 3704. Retrieved 2010/12/25.