Rapid oligosaccharide synthesis using a fluorous protective group.
The Bfp-OH, a novel fluorous protecting reagent, was able to be easily prepared. The Bfp group was readily introduced to a carbohydrate, removed in high yield, and recyclable after cleavage. The use of the Bfp group made it possible to synthesize a pentasaccharide by minimal column chromatography purification. Each synthetic intermediate was able to be easily purified only by simple fluorous-organic solvent extraction and monitored by TLC, NMR, and MS.
The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo 173-0003, Japan. tmiura@cis.ac.jp
Tsuyoshi
T
Miura
Kohtaro
K
Goto
Hideki
H
Waragai
Hiroharu
H
Matsumoto
Yuriko
Y
Hirose
Masashi
M
Ohmae
Hide-Ki
HK
Ishida
Ai
A
Satoh
Toshiyuki
T
Inazu
D002384:Catalysis; D002855:Chromatography, Thin Layer; D005461:Fluorine / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis*; D020011:Protective Agents / Q000737:chemistry*
D007202:Indicators and Reagents; D009844:Oligosaccharides; D020011:Protective Agents; D005461:Fluorine