Glycosyl phosphites as glycosylation reagents

Shin Aoki, Hirosato Kondo, Chi Huey Wong

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)


This chapter describes the application of glycosyl phosphites to the synthesis of different types of glycosides. The development of new methods for the efficient construction of glycosidic bonds is an objective of current research in carbohydrate synthesis. The practical and stereo controlled synthesis of oligosaccharides containing sialic acid, for example, remains of particular interest because of their important roles in biological recognition and cellular communication. However, the steric hindrance of the anomeric center and the ease of elimination during activation and glycosylation make the sialylation reaction particularly difficult to execute in a high-yield and stereoselective manner. A novel and high-yield sialylation using sialyl phosphite as donor and trimethylsilyltrifluoromethane sulfonate (TMSOTf) as catalyst has been illustrated in the chapter.

Original languageEnglish
Pages (from-to)193-211
Number of pages19
JournalMethods in enzymology
Issue numberC
Publication statusPublished - Jan 1 1994
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology


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