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p-Methoxyphenylglycosides

A thoughtful choice of anomeric blocking group is often of conclusive importance for the success of an oligosaccharide synthesis. The anomeric blocking group is required stability towards the reaction conditions employed and easy transformation into an activated derivative for further glycosylation.
The p-methoxyphenyl group is useful anomeric blocking group which is removed selectively by treatment with ceric ammonium nitrate, to give the corresponding glycosyl halides and thiophenyl glycosides in high yields. Furthermore, they are stable under most of the conditions used in oligosaccharide synthesis.

References

  • 1) T. Nakano, Y. Ito, T. Ogawa, Tetrahedron Lett. 1990, 31, 1597.
  • 2) M. Mori, Y. Ito, T. Ogawa, Carbohydr. Res. 1989, 192, 131.
  • 3) Y. Matsuzaki, Y. Ito, T. Ogawa, Tetrahedron Lett. 1992, 33, 4025.
  • 4) A. Dan, Y. Ito, T. Ogawa, J. Org. Chem. 1995, 60, 4680.
  • 5) C. Murakata, T. Ogawa, Carbohydr. Res. 1992, 235, 95.
  • 6) H. Kuyama, T. Nukada, Y. Nakahara, T. Ogawa, Tetrahedron Lett. 1993, 34, 2171.
  • 7) Z. Zhang, G. Mugnusson, Carbohydr. Res. 1996, 925, 41.
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