(-)-Pantoprazole

Base Information

• Chemical Name: (-)-Pantoprazole
• CAS No.: 142678-35-1
• Molecular Formula: C16H15F2N3O4S
• Molecular Weight: 383.37000
• UNII: SX78SGO2TV
• DSSTox Substance ID: DTXSID201015709
• Wikidata: Q27289440
• ChEMBL ID: CHEMBL3526697
• Mol file: 142678-35-1.mol

Synonyms:(-)-Pantoprazole;Zosecta;L-Pantoprazole;S-(-)-Pantoprazole;142678-35-1;S-Pantoprazole;SX78SGO2TV;Pantoprazole, S-;UNII-SX78SGO2TV;1H-Benzimidazole, 6-(difluoromethoxy)-2-((S)-((3,4-dimethoxy-2-pyridinyl)methyl)sulfinyl)-;6-(difluoromethoxy)-2-[(S)-(3,4-dimethoxypyridin-2-yl)methylsulfinyl]-1H-benzimidazole;(S)-(-)-Pantoprazole;PANTOPRAZOLE, (S)-;SCHEMBL29466;CHEMBL3526697;S-PANTOPRAZOLE [WHO-DD];IQPSEEYGBUAQFF-SANMLTNESA-N;DTXSID201015709;PD119113;Q27289440

Chemical Property of (-)-Pantoprazole

Chemical Property:

• PSA: 105.54000
• LogP: 3.75000
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 383.07513347
• Heavy Atom Count: 26
• Complexity: 490

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C(=NC=C1)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC(F)F)OC
• Isomeric SMILES: COC1=C(C(=NC=C1)C[S@](=O)C2=NC3=C(N2)C=C(C=C3)OC(F)F)OC
• Recent ClinicalTrials: S-pantoprazole 10mg Phase III Clinical Study

Technology Process of (-)-Pantoprazole

There total 11 articles about (-)-Pantoprazole 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: 98.3%

pantoprazole sulfide (102625-64-9) → 5‐(difluoromethoxy)‐2‐[(3,4‐dimethoxy‐2‐pyridyl)methylsulfinyl]‐1H‐benzimidazole (142678-35-1)

Guidance literature:

pantoprazole sulfide; With C₂₇H₃₁N₂O₂⁽¹⁺⁾*Br^(1-); In acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;

With 4-methylmorpholine N-oxide; In acetonitrile; at 50 ℃; for 1.5h; Reagent/catalyst; Time;

Reference yield: 87.0%

5-difluoromethoxy-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfanyl]-1H-benzimidazole → (S)-5-difluoromethoxy-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole (142678-35-1)

Guidance literature:

With dihydrogen peroxide; In water; at 25 ℃; for 3h;

Reference yield: 86.0%

→ 5‐(difluoromethoxy)‐2‐[(3,4‐dimethoxy‐2‐pyridyl)methylsulfinyl]‐1H‐benzimidazole (142678-35-1)

Guidance literature:

With manganese(II) triflate; C₃₀H₃₄N₄O₂; dihydrogen peroxide; acetic acid; In dichloromethane; at 0 ℃; for 1h;

upstream raw materials:

pantoprazole sulfide

5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole

2-Chloromethyl-3,4-dimethoxy-pyridine; hydrochloride

Refernces

• 1、 Papp, Lajos Attila,Foroughbakhshfasaei, Mohammadhassan,Fiser, Béla,Horváth, Péter,Kiss, Eszter,Sekkoum, Khaled,Gyéresi, árpád,Hancu, Gabriel,Noszál, Béla,Szabó, Zoltán-István,Tóth, Gerg?. "Reversed-phase HPLC enantioseparation of pantoprazole using a teicoplanin aglycone stationary phase—Determination of the enantiomer elution order using HPLC-CD analyses". . p. 158 - 167. Retrieved 2020.
• 2、 -. "Method for producing proton pump inhibitor compound having optical activity". Page/Page column 16; 17. . Retrieved 2019/06/15.