Syntheses and Glycosidation Reactions of 6-Thiosialosyl Donors

Hideya      Yuasa; Yoshitaka      Tanetani; Tatsuo      Miyazaki; Masayuki      Izumi; Hironobu      Hashimoto

doi:10.2174/157017808784049434

Abstract

The fluoride and thioglycoside derivatives of 6-thiosialic acid were synthesized. The thioglycoside was found to react with glycosyl acceptors in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid. Alkanols tended to be glycosylated in good yield with α-selectivity, while sugar alcohols gave only the β-glycosides in poor yields.

Keywords: Thiosugar, thioglycoside, glycosyl fluoride, sialic acid, glycosidation

« Previous Next »

Rights & Permissions Print Cite

Letters in Organic Chemistry

Title: Syntheses and Glycosidation Reactions of 6-Thiosialosyl Donors

Volume: 5 Issue: 4

Author(s): Hideya Yuasa, Yoshitaka Tanetani, Tatsuo Miyazaki, Masayuki Izumi and Hironobu Hashimoto

Affiliation:

Keywords: Thiosugar, thioglycoside, glycosyl fluoride, sialic acid, glycosidation

Abstract: The fluoride and thioglycoside derivatives of 6-thiosialic acid were synthesized. The thioglycoside was found to react with glycosyl acceptors in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid. Alkanols tended to be glycosylated in good yield with α-selectivity, while sugar alcohols gave only the β-glycosides in poor yields.

Export Options

Export File:

RIS (for EndNote, Reference Manager, ProCite)

BibTeX

Text

Content:

Citation Only

Citation and Abstract

About this article

Cite this article as:

Yuasa Hideya, Tanetani Yoshitaka, Miyazaki Tatsuo, Izumi Masayuki and Hashimoto Hironobu, Syntheses and Glycosidation Reactions of 6-Thiosialosyl Donors, Letters in Organic Chemistry 2008; 5 (4) . https://dx.doi.org/10.2174/157017808784049434