Regioselective reductive ring opening of 4-methoxybenzylidene acetals of hexopyranosides. Access to a novel protective group strategy
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 3,p. 201-202
- https://doi.org/10.1039/c39840000201
Abstract
Reduction of fully protected 4,6,-O-(4-methoxybenzylidene)hexopyranosides with sodium cyanoborohydride-trifluoracetic acid in N,N-dimethylformamide, or with trimethylsilyl chloride in acetonitrile, gives the 6-and 4-O-(4-methoxybenzyl) ethers, respectively, in good yields and with good regioselectivity; the 4-methoxybenzyl ether linkage in products containing benzyl ethers or other protective groups is selectively cleaved upon treatment with cerium(IV) ammonium nitrate in aqueous acetonitrile.Keywords
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