Protecting-Group-Free Synthesis of Glycosyl 1–Phosphates
journal contributionposted on 17.08.2012 by Landon John G. Edgar, Somnath Dasgupta, Mark Nitz
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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.