Glycosidation Reactions of 5-Thioxylopyranosyl Donors

Hideya      Yuasa; Youichiro      Suga; Hironobu      Hashimoto

doi:10.2174/157017808785740390

Abstract

Glycosidation reactions of 5-thioxylopyranosides were examined. The reaction of a 1,5-dithioxyloside derivative with N-iodosuccinimide and trifluoromethanesulfonate gave ring-opened products, but no glycosylated products. On the other hand, a 5-thioxylopyranosyl trichloroacetimidate derivative was found to react with aliphatic alcohols and a sugar alcohol to give a 5-thio analog of biologically important β(1,4)xylopyranoside structures.

Keywords: Thiosugar, thioglycoside, glycosyl donor, 5-thioxylopyranose, glycosidation

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Letters in Organic Chemistry

Title: Glycosidation Reactions of 5-Thioxylopyranosyl Donors

Volume: 5 Issue: 6

Author(s): Hideya Yuasa, Youichiro Suga and Hironobu Hashimoto

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Keywords: Thiosugar, thioglycoside, glycosyl donor, 5-thioxylopyranose, glycosidation

Abstract: Glycosidation reactions of 5-thioxylopyranosides were examined. The reaction of a 1,5-dithioxyloside derivative with N-iodosuccinimide and trifluoromethanesulfonate gave ring-opened products, but no glycosylated products. On the other hand, a 5-thioxylopyranosyl trichloroacetimidate derivative was found to react with aliphatic alcohols and a sugar alcohol to give a 5-thio analog of biologically important β(1,4)xylopyranoside structures.

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Yuasa Hideya, Suga Youichiro and Hashimoto Hironobu, Glycosidation Reactions of 5-Thioxylopyranosyl Donors, Letters in Organic Chemistry 2008; 5 (6) . https://dx.doi.org/10.2174/157017808785740390