Glucose diethyl dithioacetal hydrochloride

Solvent can have a marked effect on deamination in other respects. For example, it is commonly found that the extent of rearrangement is greater, the more polar the solvent 29,44 45 this effect is attributed to the increased lifetime of carbonium-ion species and their rearrangement to species that are more thermodynamically stable. Reactions performed at different pH values may also give different products, as illustrated by the deamination of 2-amino-2-deoxy-D-glucose diethyl dithioacetal hydrochloride in solution in (a) aqueous acetic acid and (b) hydrochloric acid (see p. 65). 

Hough, L, Taha, M I, The disulphones derived by oxidation of 2-amino-2-deoxy-D-glucose diethyl dithioacetal hydrochloride and its A-acetyl derivative with peroxypropionic acid, J. Chem. Soc., 3564-3572, 1957. 

Amino groups in dithioacetals undergo normal substitution reactions. Conventional reactions have been reported to occur with acetic anhydride,88,90,91 benzoyl chloride,46,92 l-fluoro-2,4-dinitrobenzene,250 p-toluenesulfonyl chloride,247 and benzyloxycarbonyl chloride92 the reported92 application of sodium chloride and methyl iodide to the conversion of 2-amino-2-deoxy-D-glucose diethyl dithioacetal hydrochloride into a pentamethyl derivative is presumed to be an error. Although crude 2-acetamido-2-deoxy-D-glucose diethyl dithioacetal was in one instance converted in low yield into a poorly... 

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