An expedient one-step synthesis of polysubstituted guanidinoglucosides using HgO–4 Å molecular sieves as catalyst

A novel one-step method of preparing polysubstituted guanidinoglucosides using peracetylated methyl 6-deoxy-6-thioureidoglucosides as starting materials and employing HgO in combination with molecular sieves as an efficient catalyst is reported. The structures of three methyl 2,3,4-tri-O-acetyl-6-[N2-(benzothiazol-2-yl)-N3-(oxydi-1,2-ethandiyl)]guanidino-6-deoxy-α-d-glucopyranosides were unambiguously confirmed by X-ray crystallography. The methodology affords new compounds in good yields and also provides a promising route for the synthesis of carbamate-protected guanidines.

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