Thiosugars. VI. Reaction Products of Potassium Alkyl- and Benzylxanthates with Acetylated Glucosyl Halides.

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Abstract
When potassium alkyl- or benzylxanthate was reacted on acetylated D-glucopyranosyl halides in ethanol or in acetone, acetylated D-glucopyranosyl xanthates, acetylated di-D-glucopyranosyl sulfides, and acetylated β-D-thioglucosides formed. The yield of each condensation products was affected by choice of solvent, the reaction temperature, the potassium xanthate, and starting halide used. A simple method for the preparation of bis (2, 2', 3, 3', 4, 4', 6, 6'-octa-O-acetyl-β, β'-D-glucopyranosyl) sulfide (octa-O-acetyl-isothiotrehalose) was confirmed by the reaction of potassium methyl- or benzylxanthate upon 2, 3, 4, 6-tetra-O-acetyl-α-D-glucopyranosyl bromide. Two other isomers of octa-O-acetyl-isothiotrehalose were synthesized as crystalline forms.

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