The Journal of organic chemistry

Chemistry of 1-Alkoxy-1-glycosyl Radicals: Formation of β-Mannopyranosides by Radical Decarboxylation and Decarbonylation of manno-Heptulosonic Acid …

D Crich, JT Hwang, H Yuan

Index: Crich, David; Hwang, Jae-Taeg; Yuan, Hongwei Journal of Organic Chemistry, 1996 , vol. 61, # 18 p. 6189 - 6198

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Citation Number: 43

Abstract

A method for the preparation of highly enriched β-mannopyranosides is described. A glycosyl donor 28 is prepared from tetraallyl mannonolactone by standard means and coupled to a number of primary carbohydrate alcohols, resulting in the isolation in excellent yields of axial disaccharides. Following exchange of the allyl groups for acetyl esters, the furan is oxidatively cleaved with catalytic RuO2 and NaIO4 and the resulting acid ...