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Zirconium(IV) Chloride Catalyzed New and Efficient Protocol for the Selective Cleavage of p -Methoxybenzyl Ethers

2003; American Chemical Society; Volume: 68; Issue: 11 Linguagem: Inglês

10.1021/jo026897v

1520-6904

Gangavaram V. M. Sharma, Ch. Govardhan Reddy, Palakodety Radha Krishna,

Carbohydrate Chemistry and Synthesis

A highly selective and efficient method for the unmasking of p-methoxybenzyl (PMB) ethers and esters has been developed by use of 20 mol % of zirconium(IV) chloride as Lewis acid in acetonitrile. The present method is very fast, and the conditions are tolerable to a variety of acid/base-sensitive protecting groups and substrates such as carbohydrates, terpenes, and amino acids. The products are obtained in good to high yields.