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New synthesis of C-β-D-glycopyranosylmethyl sulfides by metal-free coupling of anhydro-aldose tosylhydrazones with thiols

Abstract

Cross couplings of O-peracylated 2,6-anhydro-aldose tosylhydrazones with aliphatic, (hetero)aromatic and sugar derived thiols were studied under thermic conditions in the presence of K3PO4. The reactions with aliphatic thiols gave the corresponding C-β-D-glycopyranosylmethyl sulfides in 20-50 % yields, while 50-80 % yields were achieved with thiophenols. Sugar thiols failed to give the expected compounds with acceptable selectivity. The transformations represent a new access to these types of glycomimetic compounds. The method is complementary with the thiol-ene additions of exo-glycals (also obtained from the above tosylhydrazones) providing good yields of aliphatic and sugar derived C-glycosylmethyl sulfides. Thus, anhydro-aldose tosylhydrazones represent a common starting material toward any kind of the target compounds either in a direct coupling or via exo-glycals.

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Publication details

The article was received on 17 Aug 2017, accepted on 12 Oct 2017 and first published on 13 Oct 2017


Article type: Paper
DOI: 10.1039/C7NJ03069J
Citation: New J. Chem., 2017, Accepted Manuscript
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    New synthesis of C-β-D-glycopyranosylmethyl sulfides by metal-free coupling of anhydro-aldose tosylhydrazones with thiols

    T. Kaszás, M. Tóth and L. Somsák, New J. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7NJ03069J

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