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Totally Stereoselective synthesis of 1, 3-disaccharides through Diels-Alder reactions

A Bartolozzi, S Pacciani, C Benvenuti…

文献索引:Bartolozzi, Alessandra; Pacciani, Stefania; Benvenuti, Cecilia; Cacciarini, Martina; Liguori, Francesca; Menichetti, Stefano; Nativi, Cristina Journal of Organic Chemistry, 2003 , vol. 68, # 22 p. 8529 - 8533

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被引用次数: 16

摘要

A nonclassical, totally stereoselective synthesis of orthogonally protected 1, 3-disaccharides is reported. Enantiomerically pure β-keto-δ-lactones, efficiently obtained from glucal and galactal, are transformed into electron-poor heterodienes and chemo-, regio-, and stereoselectively cycloadded to glycals as electron-rich dienophiles, to directly afford 2- thiodisaccharides. The reductive desulfurization of the latter smoothly gave the ...