SCHEDULED MAINTENANCE
The 4,6-O-prop-2-enylidene acetals (1)–(3) on reductive cleavage with sodium cyanoborohydride–hydrogen chloride in tetrahydrofuran yield the 6-O-prop-2-enyl ethers (4), (6), and (7) in good yield. The reduction is thus compatible with the presence of glycosidic bonds, benzyl, benzoyl, and acetamido-groups and gives ready access to protected hexopyranosides with free 4-hydroxy-group.
P. J. Garegg, H. Hultberg and S. Oscarson, J. Chem. Soc., Perkin Trans. 1, 1982, 2395 DOI: 10.1039/P19820002395
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