O-Benzyl-L-valine toluene-p-sulphonate
L-Valine benzyl ester p-toluenesulfonate (CAS 16652-76-9), commonly written H-Val-OBzl.TosOH, is the crystalline tosylate salt of the benzyl ester of L-valine. It is a white to off-white solid melting near 160 to 162 degrees Celsius, soluble in polar organic solvents such as methanol, ethanol, dichloromethane and dimethylformamide, and it is stable when kept dry and cool. The benzyl ester protects the carboxyl group of valine during peptide coupling and can later be removed cleanly by catalytic hydrogenolysis or strong acid, while the tosylate counter-ion keeps the amino function protonated, non-nucleophilic and crystalline. The defined L configuration guarantees stereochemical integrity, and the salt form makes accurate weighing straightforward.
1. Peptide synthesis: used as a protected amino acid building block for introducing L-valine residues into peptides, peptide drugs and peptidomimetics in solution and solid-phase synthesis, and in fragment condensation strategies.
2. Protecting-group strategy: the benzyl ester is stable to the acid and base conditions of chain assembly and is selectively cleaved by hydrogenolysis or strong acid, allowing orthogonal protection schemes with Boc, Fmoc and tert-butyl groups.
3. Pharmaceutical intermediate: applied in the manufacture of active pharmaceutical ingredients and chiral auxiliaries where an enantiopure valine unit is required, including antiviral, antihypertensive, immunosuppressant and anticoagulant products containing valine residues.
4. Handling and storage: not classified as hazardous under normal use but irritating as a dust; keep containers sealed and dry at ambient temperature away from strong oxidising agents, and protect the ester from hydrolysis under strongly basic conditions.
Product Name: O-Benzyl-L-valine toluene-p-sulphonate
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