Glycosyl Sulfoxides in Glycosylation Reactions

  • Jing Zeng
  • Yan Liu
  • Wei Chen
  • Xiang Zhao
  • Lingkui Meng
  • Qian WanEmail author
Part of the following topical collections:
  1. Sulfur Chemistry


Carbohydrate chemistry has benefited a lot from the intrinsic reactivity of sulfoxide since it was introduced in glycosylation reactions by Kahne in 1989. Since then, extensive studies have been explored by employing sulfoxide as glycosyl donors and activation reagents in construction of glycosidic bonds. As glycosyl donors, the sulfinyl groups could locate either directly or remotely at anomeric position. This chapter focuses on the establishment and development of sulfoxides as glycosyl donors in glycosylation reactions, with an emphasis on their applications and postulated mechanisms.


Sulfoxide Carbohydrate Glycosylation 







Contact ion pairs
















Intramolecular aglycon delivery


Lithium aluminum hydride


3-chloroperbenzoic acid


















Solven-separated ion pairs








Trifluoromethanesulfonic anhydride




Trifluoromethanesulfonic acid






Trimethylsilyl trifluoromethanesulfonate




β-domain of human follicle-stimulating hormone



We thank the National Natural Science Foundation of China (21672077, 21772050, 21472054, 21702068), the State Key Laboratory of Bioorganic and Natural Products Chemistry (SKLBNPC13425), Natural Science Funds of Hubei Province for Distinguished Young Scholars (2015CFA035), Wuhan Creative Talent Development Fund, “Thousand Talents Program” Young Investigator Award, and Huazhong University of Science and Technology for support.


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© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.School of PharmacyHuazhong University of Science and TechnologyWuhanChina
  2. 2.Institute of Brain ResearchHuazhong University of Science and TechnologyWuhanChina

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