Tebipenem

Base Information

• Chemical Name: Tebipenem
• CAS No.: 161715-21-5
• Molecular Formula: C16H21N3O4S2
• Molecular Weight: 383.492
• UNII: Q2TWQ1I31U
• DSSTox Substance ID: DTXSID40167227
• Nikkaji Number: J1.535.394E
• Wikipedia: Tebipenem
• Wikidata: Q27286930
• ChEMBL ID: CHEMBL576981
• Mol file: 161715-21-5.mol

Synonyms:SPR994;tebipenem

Chemical Property of Tebipenem

Chemical Property:

• Boiling Point: 624.5±65.0 °C(Predicted)
• PKA: 4.29±0.60(Predicted)
• PSA: 144.04000
• Density: 1.75
• LogP: -0.02830
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: insoluble in EtOH; ≥19.15 mg/mL in H2O with gentle warming; ≥24.9 mg/mL in DMSO
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 383.09734851
• Heavy Atom Count: 25
• Complexity: 689

Purity/Quality:

97% ^*data from raw suppliers

Tebipenem ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C(C(=O)N2C(=C1SC3CN(C3)C4=NCCS4)C(=O)O)C(C)O
• Isomeric SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1SC3CN(C3)C4=NCCS4)C(=O)O)[C@@H](C)O

Technology Process of Tebipenem

There total 11 articles about Tebipenem 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: 94.5%

(+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-{[1-(2-thiazolin-2-yl)-3-azetidinyl]sulfanyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid-p-nitrobenzyl ester (161715-20-4) → Tebipenem (161715-21-5)

Guidance literature:

With hydrogen; In water; butan-1-ol; at 20 ℃; for 4h; under 15001.5 Torr; Solvent; Pressure; Reagent/catalyst;

Reference yield: 78.9%

C19H25N3O4S2 → Tebipenem (161715-21-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; In water; at 13 ℃; for 2.5h; under 11251.1 Torr; Large scale;

Reference yield: 77.0%

(4R,5S,6S)-3-((1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl)thio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carbonyl 4-nitrobenzoate → Tebipenem (161715-21-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; In water; butan-1-ol; at 20 ℃; for 7h; under 3000.3 - 3750.38 Torr; Solvent; Pressure; Temperature;

upstream raw materials:

(+)-(4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-{[1-(2-thiazolin-2-yl)-3-azetidinyl]sulfanyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid-p-nitrobenzyl ester

3-methanesulfonyloxy-1-(1,3-thiazolin-2-yl)azetidine

1-(1,3-thiazolin-2-yl-)azetidin-3-ol

3-acetylthio-1-(1,3-thiazolin-2-yl)azetidine

Downstream raw materials:

tebipenem