Totally stereoselective synthesis of 1,3-disaccharides through Diels-Alder reactions |
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| Authors: | Bartolozzi Alessandra Pacciani Stefania Benvenuti Cecilia Cacciarini Martina Liguori Francesca Menichetti Stefano Nativi Cristina |
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| Institution: | Dipartimento di Chimica Organica Ugo Schiff, Universita' di Firenze, and CNR-ICCOM, via della Lastruccia, 13 I-50019 Sesto Fiorentino (FI), Italy. |
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| Abstract: | A nonclassical, totally stereoselective synthesis of orthogonally protected 1,3-disaccharides is reported. Enantiomerically pure beta-keto-delta-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 corresponding 2,2'-dideoxydisaccharides. |
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