(R)-Glycidyl tosylate

white crystalline powder

Paratoluenesulfonyl chloride (PTSC, 25.0 g) and (R)-oxiran-2-ylmethanol (6.0 mL) were dissolved in anhydrous dichloromethane (DCM, 250 mL), then, triethylamine (TEA, 36.0 mL) was dropwise added in the mixture at 0 °C. Tosyl chloride (25.0 g) was dissolved in redissolved dichloromethane (250 mL) and (R)-glycidol (6.0 mL) was added to the solution.Triethylamine (36.0 mL) was added dropwise to the reaction solution at 0° C. The reaction was carried out for 3 hours, evaporated to dryness and passed through the column. This gave 17.6 g of a white solid with a yield of 85.0percent.Example 4 To 1.2 L of a methylene chloride solution of (R)-3-chloro-l, 2-propanediol (200g, 99.5percent ee) was added 499 g of potassium phosphate tribasic, and then the obtained solution was refluxed, under stirring, for 3 hours. The resulting solution was cooled to 0°C, and 201 g of triethylamine, 4 g of 4-(dimethylamino)pyridine, and tosyl chloride (69 g x 5) was added to the solution. After additional stirring for 1 hour at a room temperature, the reaction mixture was successively washed with 2.2 L of 5percent aqueous potassium carbonate solution, 2 L of IN aqueous hydrogen chloride solution, and 1 L of water. The organic layer was dried with 50 g of anhydrous sodium sulfate and filtrated. Evaporation of the methylene chloride under reduced pressure gave a crude product (chemical purity: 99.3percent, optical purity 99.5percent ee). After addition of hexane to the resulting residue, the obtained solid product was filtrated to give 337 g of the targeted product:-Yield: 81.5percent- Chemical purity: 99.8percent- Optical purity (GC) 99.5percent ee- Melting point: 47~49°C

Protected Glycidol, used as an intermediate in the preparation of neurochemicals.

Molecular Weight:228.27
XLogP3:1.1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:228.04563003
Monoisotopic Mass:228.04563003
Topological Polar Surface Area:64.3
Heavy Atom Count:15
Complexity:298
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes