A nonclassical, totally stereoselective synthesis of orthogonally protected 1,3-disaccharides is reported. Enantiomerically pure â-keto-ä-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.

Totally Stereoselective Synthesis of 1,3-Disaccharides through Diels-Alder Reactions / A. BARTOLOZZI; S. PACCIANI; C. BENVENUTI; M. CACCIARINI; F. LIGUORI; S. MENICHETTI; C. NATIVI. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - STAMPA. - 68:(2003), pp. 8529-8533. [10.1021/jo034556r]

Totally Stereoselective Synthesis of 1,3-Disaccharides through Diels-Alder Reactions

CACCIARINI, MARTINA;MENICHETTI, STEFANO;NATIVI, CRISTINA
2003

Abstract

A nonclassical, totally stereoselective synthesis of orthogonally protected 1,3-disaccharides is reported. Enantiomerically pure â-keto-ä-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.
2003
68
8529
8533
A. BARTOLOZZI; S. PACCIANI; C. BENVENUTI; M. CACCIARINI; F. LIGUORI; S. MENICHETTI; C. NATIVI
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/308794
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