Abstract
Hydrogen peroxide-trichloroacetic acid is an effective reagent combination for the mild cleavage of acid-labile protective groups.
Highlights
We have found that the tetrahydropyranyl group of 5 (9 h, 8O%)t and the trityl group of 6 (24 h, 85%)5 are smoothly removed under similar reaction conditions, suggesting potential for wider application of the method in the removal of acid-labile protective groups and indicating that complications arising from free-radical or peracid impurities are, at best, minor
In the course of research directed towards a synthesis of neocarzinostatin chromophore and related compounds, we required a means to transform the dimethyl acetall into the aldehyde 2.1 An extensive survey of aqueous acid-cosolvent combinations failed to reveal conditions which would effect hydrolysis of the dimethyl acetal group of 1 without competitive opening of the epoxide ring
The ability of hydrogen peroxide to enter into acetal exchange reactions has long been recognized, though reported reaction conditions2 have perhaps dissuaded wider exploration of the method
Summary
We have found that the tetrahydropyranyl group of 5 (9 h, 8O%)t and the trityl group of 6 (24 h, 85%)5 are smoothly removed under similar reaction conditions, suggesting potential for wider application of the method in the removal of acid-labile protective groups and indicating that complications arising from free-radical or peracid impurities are, at best, minor. Mild conditions for the removal of acid-labile protective groups. Pergamon Press plc MILD CONDITIONS FOR THE REMOVAL OF ACID-LABILE PROTECTIVE GROUPSt
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