Pseudothiouronium salts

An acylated glycosyl halide, such as a 2,3,4,6-tetra-O-acetyl derivative, is treated with thiourea. The resulting pseudothiouronium salt is hydrolyzed with aqueous potassium carbonate to give the 2,3,4,6-tetra-0-acetyl-l-thio-(3-D-glucopyranose,48 which then is alkylated. 

Reaction of a>-(phthalimidooxy)alkyl bromides with pseudothiourea to give 2-[[Pg.347]

Reaction of thiourea with 2-haloacetamides and 2-haloacetates to give pseudothiouronium salts and pseudothiohydantoins [85],... 

Indirect formation of thioglycosides can also be performed from glycosyl halides. Reaction with thiourea yields a pseudothiouronium salt, which (as the thioacetate above) can be hydrolyzed under mild, selective conditions to give the anomeric thiol, which then can be alkylated in an efficient, non-smelling procedure to produce... 

Pseudoacids s. Hydroxylactones Pseudoaromatic rings s. Dithio-lium salts. Metal complex compounds, Tropenium salts Pseudoindoles s. 2-Chloro-3,3-dimethylindolenine Pseudothiouronium salts s. Isothiouronium salts Pumice 16, 210 Pummerer reaction 15, 177 Purines... 

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