Pyridinium p-Toluenesulfonate

Chemical properties

white to light beige crystalline powder or

The Uses of Pyridinium p-Toluenesulfonate

Pyridinium p-Toluenesulfonate is used in the synthesis of a subdomain of the cytochrome P450 BM3 enzyme, for use in screening systems for drug candidates.

Preparation

To a flask containing the SM (13.15 g, 52.8 mmol) in dry DCM (90 mL) was added 3,4-dihydro-2H-pyran (10 mL, 110 mmol) followed by pyridinium p-TsOH (0.13 g, 0.53 mmol).  The reaction mixture was stirred at a gentle reflux (50 C) for 24 h  (monitored by TLC and LCMS). The mixture was concentrated in vacuo. The  resulting material was diluted with MeOH and heated in a flask on a rotovap  (without vacuum) at 40 C for about 30 min. The mixture was  concentrated to about 5 mL in volume, cooled to RT, and filtered. The resulting  white solid was rinsed with MeOH (1x) to provide the product. [13.35 g, 76%]

The Uses of Pyridinium p-Toluenesulfonate

As a co-catalyst with L-proline improved both yield and enantioselectivity of an asymmetric aldol condensation between dioxanones and aldehydes.1

The Uses of Pyridinium p-Toluenesulfonate

Pyridinium p-Toluenesulfate serves as an efficient catalyst for the preparation of tetrahydropyranyl ethers, which are essential for the protection of hydroxyl groups (OH-protection). This application utilizes DHP, with the specific catalyst referenced by the catalog number D106208.

Furthermore, when used in conjunction with L-proline as a co-catalyst, Pyridinium p-Toluenesulfate enhances the yield and enantioselectivity of asymmetric aldol condensation reactions between dioxanones and aldehydes.

Flammability and Explosibility

Not classified