Glycosyl phosphates oligosaccharides using

Solid-Phase Oligosaccharide Synthesis Using Glycosyl Phosphates... 

Plante OJ, Andrade RB, Seeberger PH. Synthesis and use of gly-cosyl phosphates as glycosyl donors. Org. Lett. 1999 1 211-214. Plante OJ, Palmacci ER, Andrade RB, Seeberger PH. Oligosaccharide synthesis with glycosyl phosphate and dithiophosphate triesters as glycosylating agents. J. Am. Chem. Soc. 2001 123 9545-9554. 

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. 

Fraser-Reid et al. [21,22] reported the synthesis of polymer supported oligosaccharides using n-pentenyl glycosides, while Seeberger et al. [23] accomplished the synAesis of p-(l- 4)- and p.(2 6)-linked ohgosaccharides using glycosyl phosphates combined with an octenediol linker. 

Table 11.2-1 General cycle used with glycosyl phosphates for the construction of oligosaccharides 1-3...

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. 

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