Stereocontrolled Glycoside and Glycosyl Ester Synthesis. Neighboring Group Participation and Hydrogenolysis of 3-(2‘-Benzyloxyphenyl)-3,3-dimethylpropanoates
- 9 March 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (8) , 1613-1615
- https://doi.org/10.1021/ol070449y
Abstract
The 2-O-[3-(2‘-benzyloxyphenyl)-3,3-dimethylpropanoate] and 2-O-[3-(2‘-benzyloxy-4‘,6‘-dimethylphenyl)-3,3-dimethylpropanoate] esters enable the synthesis of a range of β-glucosides and α-mannosides through neighboring participation in excellent yield, and are removed by hydrogenolysis in concert with the cleavage of benzyl esters in the presence of other esters making them particularly well suited to the stereocontrolled synthesis of glycosyl esters.Keywords
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