Preparative Organic Chemistry
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ChemInform Abstract: Selective Deoxygenation of Unsaturated Carbohydrates with Pd(0)/ Ph2SiH2/ZnCl2. Total Synthesis of (+)-(S,S)-(6-Methyltetrahydropyran-2-yl)acetic Acid.
First published: February 7, 1989
Abstract
The glycals (I) and (IIIa) are reduced with diphenylsilane in the presence of zinc chloride and a Pd(0) catalyst, yielding the deacetoxylated derivatives (II) or (IV).
ChemInform Abstract
The glycals (I) and (IIIa) are reduced with diphenylsilane in the presence of zinc chloride and a Pd(0) catalyst, yielding the deacetoxylated derivatives (II) or (IV). The 2,3-unsaturated pyranosides (V) yield mixtures of the 2,3- (VII) and 3,4-anhydro sugars (VIII). The method is also applied to the synthesis of the methyltetrahydropyranylacetic acid (XIV). Numerous further examples are given in the original paper. Labeling experiments using dideuteriodiphenylsilane are also performed.
