A 5-Ureido-Modified Sialyl Donor: A Tool for the Synthesis of alpha-Sialosides

作者:Tanase Maiko; Imamura Akihiro*; Ando Hiromune; Ishida Hideharu; Kiso Makoto*
来源:Organic Letters, 2016, 18(6): 1454-1457.
DOI:10.1021/acs.orglett.6b00403

摘要

A novel method for the synthesis of alpha-sialosides using a newly developed 5-ureido-modified sialyl donor is reported. The donor was found to be useful for alpha-selective sialidation with various glycosyl acceptors, forming alpha(2,6)Glc, alpha(2,6)Gal, and alpha(2,3)Gal linkages in excellent yield and with stereoselectivity. Furthermore, alpha-sialoside was easily isolated from the reaction mixture by the 1,5-lactamization method under mild conditions. Successful application of the C5-ureido sialyl donor to the synthesis of a sialoside confirmed the usefulness of the present method.

  • 出版日期2016-3-18