ol3019083_si_001.pdf (17.37 MB)

Protecting-Group-Free Synthesis of Glycosyl 1–Phosphates

Download (17.37 MB)
journal contribution
posted on 17.08.2012 by Landon John G. Edgar, Somnath Dasgupta, Mark Nitz
Glycosyl 1-phosphates enriched in the α-anomer are obtained without the use of protecting groups in two steps starting from the free hemiacetal. Condensation of free hemiacetals with toluenesulfonylhydrazide yields a range of glycosylsulfonohydrazide donors which can be oxidized using cupric chloride in the presence of phosphoric acid and the coordinating additive 2-methyl-2-oxazoline to give useful yields of the fully deprotected glycosyl 1-phosphates.