Solid-Phase Oligosaccharide Synthesis Using Glycosyl Phosphates

Solid-Phase Oligosaccharide Synthesis Using Glycosyl Phosphates 

WILM-CHRISTIAN HAASE, OBADIAH J. PLANTE, and PETER H. SEEBERGER 

2 Special Applications of Glycosyl Phosphates in Oligosaccharide Synthesis 

C-Glycosidic linkages are present in various natural products and may inhibit glycosidases due to the structural analogy to their O-counterparts.42 Glycosyl phosphates 63 and 48 served successfully in the a-selective synthesis of aryl 

Direct nucleophilic displacements of the phosphate leaving group in inert organic solvents by nucleophiles of the 

---

This chapter desribes the synthesis of glycosyl phosphates and their use as glycosylating agents. Their use in die construction of complex oligosaccharides, both in solution and on solid support, is presented. Their ease of synthesis in combination with their rapid activation have made them ideal glycosylating agents to be used for automated solid phase oligosaccharide synthesis. 

Most frequently, diphenyl and di-n-butyl phosphates are used. As such, Singh and coworkers [471-474] introduced the cyclic propane-1,3-diyl phosphates. Additionally, Seeberger and coworkers [277,475-482] have recently applied glycosyl phosphates for the synthesis of various oligosaccharides both in solution and in solid-phase syntheses. 

---