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Note | Regular issue | Vol 81, No. 7, 2010, pp.1711-1720
Published online, 1st June, 2010
DOI: 10.3987/COM-10-11974
Synthesis of Galacto- and Mannosucroses

Atsushi Ueda, Takanori Yamashita, and Jun'ichi Uenishi*

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan


A concise synthesis of β-D-fructofuranosyl α-D-galactopyranoside (2), and β-D-fructofuranosyl α-D-mannopyranoside (3) is described. Inversion of the C-3 α-hydroxy group of α-D-galactopyranosyl and α-D-mannopyranosyl β-D-psicofuranosides 10 and 11 via oxidation and stereoselective reduction furnished the corresponding β-D-fructofuranosides in excellent yields.