Synthesis 2008(5): 770-776  
DOI: 10.1055/s-2008-1032183
PAPER
© Georg Thieme Verlag Stuttgart · New York

Versatile and Mild Synthesis of Di- and Trisaccharidic 2-Enopyranosyl ­Cyanides by Cyanation of Per-O-acetylglycals with Trimethylsilyl Cyanide Catalyzed by Palladium(II) Acetate

Xiaoyong Xua,b,1, Qitao Tana,b, Masahiko Hayashi*b
a Department of Frontier Research and Technology, Headquarters for Innovative Cooperation and Development, Kobe University, Nada, Kobe 657-8501, Japan
b Department of Chemistry, Graduate School of Science, Kobe University, Nada, Kobe 657-8501, Japan
Fax: +81(78)8035688; e-Mail: mhayashi@kobe-u.ac.jp;
Further Information

Publication History

Received 29 October 2007
Publication Date:
18 February 2008 (online)

Abstract

A catalytic amount (1-2 mol%) of palladium(II) acetate was found to work as a catalyst for the cyanation of di- and tri­saccharidic per-O-acetylglycals with trimethylsilyl cyanide to afford di- and trisaccharidic 2-enopyranosyl cyanides in high yields and in moderate stereoselectivities.

1

Present address: Shanghai Key Lab of Chemical Biology, School of Pharmacy, East China University of Science and Technology, P.O. Box 544, Shanghai 200237, P. R. of China.