Stereocontrolled Glycoside and Glycosyl Ester Synthesis. Neighboring Group Participation and Hydrogenolysis of 3-(2‘-Benzyloxyphenyl)-3,3-dimethylpropanoates
journal contributionposted on 12.04.2007, 00:00 by David Crich, Feng Cai
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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.