Direct C-glycosylation of indole with unprotected mono-, di-, and trisaccharides: a one-pot synthesis of 1-deoxy-1,1-bis(3-indolyl)alditols.
1-Deoxy-1,1-bis(3-indolyl)alditols were synthesized by reacting 2.5equiv of indole with 1equiv of the following seven monosaccharides (D-galactose, D-mannose, D-allose, 2-deoxy-D-arabinohexose (2-deoxy-D-glucose), D-arabinose, L-arabinose, D-xylose), two disaccharides (D-lactose, D-maltose), and a trisaccharide (D-maltotriose) in 1:1 EtOH-H(2)O at room temperature, or at 40 or 50 degrees C, in the presence of 5 mol% scandium(III) trifluoromethanesulfonate [Sc(OTf)(3)], in a one-pot reaction, in 36-95% yields.
Sato
Shingo
S
Faculty of Engineering, Yamagata University, 4-3-16 Jonan, Yonezawa-shi, Yamagata 992-8510, Japan. shingo-s@yz.yamagata-u.ac.jp <shingo-s@yz.yamagata-u.ac.jp>
Masukawa
Hiroya
H
Sato
Toshihiro
T
D004187:Disaccharides / Q000737:chemistry; D006031:Glycosylation; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry; D009005:Monosaccharides / Q000737:chemistry; D012538:Scandium / Q000737:chemistry; D013402:Sugar Alcohols / Q000138:chemical synthesis*; D014312:Trisaccharides / Q000737:chemistry
D004187:Disaccharides; D007211:Indoles; D008698:Mesylates; D009005:Monosaccharides; D013402:Sugar Alcohols; D014312:Trisaccharides; C436603:scandium triflate; C030374:indole; D012538:Scandium