L-(-)-O-TOSYLLACTIC ACID ETHYL ESTER

The L-(-)-O-Tosyllactic acid ethyl ester, with the CAS registry number 57057-80-4, is also known as Propanoic acid, 2-[[(4-methylphenyl)sulfonyl]oxy]-, ethyl ester, (2S)-. It belongs to the product categories of Chiral Building Blocks; Esters (Chiral); Synthetic Organic Chemistry. This chemical's molecular formula is C₁₂H₁₆O₅S and molecular weight is 272.32. What's more, its systematic name is called Ethyl (2S)-2-{[(4-methylphenyl)sulfonyl]oxy}propanoate.

Physical properties about L-(-)-O-Tosyllactic acid ethyl ester are: (1) ACD/LogP: 1.92; (2) # of Rule of 5 Violations: 0; (3) ACD/LogD (pH 5.5): 2; (4) ACD/LogD (pH 7.4): 2; (5) ACD/BCF (pH 5.5): 32; (6) ACD/BCF (pH 7.4): 32; (7) ACD/KOC (pH 5.5): 413; (8) ACD/KOC (pH 7.4): 413; (9) #H bond acceptors: 5; (10) #H bond donors: 0; (11) #Freely Rotating Bonds: 6; (12) Polar Surface Area: 78.05 Å²; (13) Index of Refraction: 1.51; (14) Molar Refractivity: 66.92 cm³; (15) Molar Volume: 223.734 cm³; (16) Surface Tension: 40.872 dyne/cm; (17) Density: 1.217 g/cm³; (18) Flash Point: 186.231 °C; (19) Enthalpy of Vaporization: 63.298 kJ/mol; (20) Boiling Point: 384.321 °C at 760 mmHg; (21) Vapour Pressure: 0 mmHg at 25 °C.

Preparation of L-(-)-O-Tosyllactic acid ethyl ester: this chemical can be prepared by Toluene-4-sulfonyl chloride with (R)-2-Hydroxy-propionic acid ethyl ester.

This reaction needs reagent Triethylamine at ambient temperature. The reaction time is 9 hours. The yield is 70 %.

Uses of L-(-)-O-Tosyllactic acid ethyl ester: it can react with Propionic acid; potassium propionate to give Ethyl (R)-2-propionoxypropionate.

The reaction occurs with reagent Acetonitrile and other condition of heating for 18 hours. The yield is 73 %.

You can still convert the following datas into molecular structure:
(1) SMILES: O=S(=O)(O[C@H](C(=O)OCC)C)c1ccc(cc1)C
(2) InChI: InChI=1/C12H16O5S/c1-4-16-12(13)10(3)17-18(14,15)11-7-5-9(2)6-8-11/h5-8,10H,4H2,1-3H3/t10-/m0/s1
(3) InChIKey: SNLMUZGICZJWKN-JTQLQIEIBR