A new, iterative strategy of oligosaccharide synthesis based on highly reactive beta-bromoglycosides derived from selenoglycosides.
Stereoselective conversion of a selenoglycoside to a beta-bromoglycoside in the absence of a glycosyl acceptor followed by the coupling with another selenoglycoside affords the corresponding glycosylated selenoglycoside, which could be directly used for the next glycosylation. The iteration of this sequence allows the synthesis of a variety of oligosaccharides including an elicitor active heptasaccharide. [reaction: see text]
Yamago
S
S
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan. yamago@sbchem.kyoto-u.ac.jp
Yamada
T
T
Hara
O
O
Ito
H
H
Mino
Y
Y
Yoshida
J I
JI
D001966:Bromine / Q000737:chemistry*; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000737:chemistry*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D018036:Selenium Compounds / Q000737:chemistry*
D006027:Glycosides; D009844:Oligosaccharides; D018036:Selenium Compounds; D001966:Bromine