The reaction of 2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactosyl isothiocyanate (1) with 2-amino-4/6-substituted benzothiazoles 2a-2e gave lactosylthioureas 3a-3e, which were treated with amines in the presence of HgCl2 to afford a series of novel N-alkyl/aryl-N'-(4/6-substituted benzothiazol-2-yl)-N''-perace-tylated lactosylguanidines 4-6.

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.

The nucleophilic addition of rhamnosyl isothiocyanate to substituted 2-aminobenzothiazoles (2a～2f), 2-hydrazinobenzothiazoles (2g～2l), oxidized and nonoxidized 3-hydra- zinocarbon.

Refluxing of 2 with glucosyl isothiocyanate(1)in CHCl_3 gave corresponding N,N′-substituted-N″-(2,3,4,6-tetra-O-acetylglucosylthioureylene)phosphoric triamides(3a-3g),and deacetylation in MeOH/NaOMe gave N,N'-substituted-N″-glucosy1 thioureylene phosphoric triamides(4a-4g).

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).