Beilstein J. Org. Chem.2013,9, 135–146, doi:10.3762/bjoc.9.16
)oxadiazolinethiones showed a ring opening of the oxadiazoline ring (without affecting the glycosyl moiety) to give N-(glycosyl)thiosemicarbazides. Herewith, a new synthetic access to one of the four classes of glycosylthiosemicarbazides was found. The ultimate confirmation of new structures was achieved by X-ray
: glycosyloxadiazolinethiones; glycosylsulfanyloxadiazoles; glycosylthiosemicarbazides; thermal rearrangement; X-ray crystallography; Introduction
Modified nucleosides are versatile motifs for studying the relationship between the structure and functions of nucleic acids and problems of metabolism, besides their main
][4][5][6][7], such as glycosylisothiocyanates, which afford glycosylthiosemicarbazides [8] or glycosyl 3-thioureidothiourea derivatives [9]. These 4-N-(glycosyl)thiosemicarbazides [8] were used for the synthesis of Schiff-like bases [10] and 4-N-glycosyl(thiosemicarbazido)phosphorothionates as
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Graphical Abstract
Scheme 1:
Structures of the different glycosylthiosemicarbazides.