Totally Stereoselective synthesis of 1, 3-disaccharides through Diels-Alder reactions
A Bartolozzi, S Pacciani, C Benvenuti…
Index: 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
Full Text: HTML
Citation Number: 16
Abstract
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 ...
Related Articles:
Stereocontrolled Total Synthesis of Polygalolide A
[Yamada, Hitomi; Adachi, Masaatsu; Isobe, Minoru; Nishikawa, Toshio Chemistry - An Asian Journal, 2013 , vol. 8, # 7 p. 1428 - 1435]
Stereocontrolled Total Synthesis of Polygalolide A
[Yamada, Hitomi; Adachi, Masaatsu; Isobe, Minoru; Nishikawa, Toshio Chemistry - An Asian Journal, 2013 , vol. 8, # 7 p. 1428 - 1435]
[Capozzi, Giuseppe; Giannini, Sabrina; Menichetti, Stefano; Nativi, Cristina; Giolitti, Alessandro; Patacchini, Riccardo; Perrotta, Enzo; Altamura, Maria; Alberto Maggi, Carlo Bioorganic and Medicinal Chemistry Letters, 2002 , vol. 12, # 17 p. 2263 - 2266]
Stereocontrolled Total Synthesis of Polygalolide A
[Yamada, Hitomi; Adachi, Masaatsu; Isobe, Minoru; Nishikawa, Toshio Chemistry - An Asian Journal, 2013 , vol. 8, # 7 p. 1428 - 1435]
Direct 3, 6-di-O-protection of glucal and galactal
[Kinzy, Willy; Schmidt, Richard R. Tetrahedron Letters, 1987 , vol. 28, # 18 p. 1981 - 1984]