The reaction of 2,3,4-tri-O-acetyl-β-D-xylopyranosyl isothiocyanate 1 and 2-amino-4/6-substituted benzothiazoles 2a～2e gave xylopyranosylthioureas 3a～3e,which then reacted with alkyl/aryl amine in the presence of HgCl_2 to afford a series of new guanidinoxylopyranosides (4a～4e,5a～5e,6a～6e and 7a～7e).

Separation of Amine Enantiomer by High Performance Liquid Chromatography with D-Glycosyl-isothiocyanate as Pre-column Derivatizing Reagent;

Eight novel compounds of 2 aryl 5 ( N 2′,3′,4′,6′ tetra O acetyl β D glucopyranosyl) imido 1,3,4 thiadiazolinesⅣ a～h were synthesized from 2,3,4,6 tetra O acetyl β D glucopyranosyl isothiocyanate via 3 step reactions, i.

Tetra-O-acetyl-β-D-glycosyl isothiocyanate was synthesized using α-D-glucose as the starting material through three step reactions and characterized by NMR.

Fifteen target compounds were synthesized with the following three steps: amino acids were protected to form carbobenzoxyamino acid methyl esters, the carbobenzoxyamino acid methyl esters reacted with hydrazine to give carbobenzoxy amino acid hydrazides, and treatment of the carbobenzoxy amino acid hydrazides with glycosyl isothiocyanates afforded 3a～3o in 65%～86% yields.

The reaction of 2 with glycosyl isothiocyanates 3～5 gave the novel compounds, N-glycosyl-N'-amido thioureas 6～8.

The glycosyl isothiocyanates 1a～1c reacted with anhydrous hydrazine gave N-glycosyl- N'-aminothioureas 2a～2c, which then reacted further with 6-substituted-3-formylchromones 3a～3d to give a series of new N-glycosyl-N′-6-substitutedchromon-3-ylmethylideneaminothioureas 4a～4d, 5a～5d, 6a～ 6d.