142706-18-1

Basic information

• Product Name: (+)-(R)-Pantoprazole
• Synonyms: (+)-(R)-Pantoprazole;Pantoprazole Isomer(R) Impurity
• CAS NO: 142706-18-1
• Molecular Formula: C16H15F2N3O4S
• Molecular Weight: 383.3698064
• Mol File: 142706-18-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 586.9±60.0 °C(Predicted)
• Appearance: /
• Density: 1.51±0.1 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.33±0.10(Predicted)
• CAS DataBase Reference: (+)-(R)-Pantoprazole(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(R)-Pantoprazole(142706-18-1)
• EPA Substance Registry System: (+)-(R)-Pantoprazole(142706-18-1)

Safety Data

• Hazardous Substances Data: 142706-18-1(Hazardous Substances Data)

Usage

Uses

(R)-(+)-Pantoprazole is the R-enantiomer of Pantoprazole (P183000), an antiulcerative. Gastric pump inhibitor.

Upstream product

• 102625-64-9 pantoprazole sulfide 
• 97963-62-7 5-(difluoromethoxy)-2-mercapto-1H-benzimidazole 

Relevant articles and documents

Synthesis of Esomeprazole and Related Proton Pump Inhibitors through Iron-Catalyzed Enantioselective Sulfoxidation

We report here an application of iron catalysis for the kilogram scale asymmetric synthesis of a proton pump inhibitor, esomeprazole, in 87% yield and 99.4% ee by catalytic sulfoxidation with hydrogen peroxide using an iron salt/chiral Schiff base in combination with a carboxylate salt. Under similar reaction conditions, other proton pump inhibitors such as (S)-lansoprazole, (S)-rabeprazole, and (S)-pantoprazole, were also synthesized in high yield and ee. A carboxylate additive was crucial for the success of this reaction, and we consider that it coordinates to the active iron species, and it also acts as a hydrogen-bond acceptor to coordinate to the substrate through the imidazole NH.

Biphasic recognition chiral extraction - Novel way of separating pantoprazole enantiomers

This paper presents a biphasic recognition chiral extraction system developed as a new chiral separation technology for the separation of pantoprazole enantiomers, combining a hydrophilic β-CD derivative in the aqueous phase and a hydrophobic tartaric acid in the organic phase which preferentially recognise the (R)-enantiomer and (S)-enantiomer, respectively. In this study, a number of factors which influence the efficiency of the extraction were investigated including types of organic solvents, β-CD and tartaric acid esters and their concentrations, pH and temperature. As a result, enantioselectivity for pantoprazole enantiomers can be improved up to 1.42 under optimised conditions; in addition, it is clear that the combined action of β-CD and tartaric acid esters leads to formation of the biphasic chiral extraction system with a stronger separation capacity than a monophasic chiral extraction system.