[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]thiourea

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl bromopyruvate (8.99 g., 0.047 mole) was added to a suspension of N-β-D-glucopyranosylthiourea (10 g., 0.042 mole) in 120 ml. of hot ethanol, and the reaction was completed by heating 30 minutes. During the heating, the mixture became a clear solution. The reaction solution was evaporated to dryness in vacuo. The residue was crystallized from ethanol and acetone, filtered, and dried at room temperature in vacuo, yielding 16.03 g. (91.9%); white powder; m.p. 162°-163°(dec.). by heating 30 minutes The reaction solution was evaporated to dryness in vacuo The residue was crystallized from ethanol and acetone filtered dried at room temperature in vacuo yielding 16.03 g

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-(2,3,4,6-Tetra-O-acetyl-β-D glucopyranosyl)-5-benzylidenerhodanine(5.52 g., 0.01 mole) was added to a solution of 50 ml. of methanol saturated with ammonia at 0° in a pressure bottle. The mixture was stirred at room temperature for 18 hours with the stopper well closed. The mixture was evaporated to a syrupy material below 30° in vacuo. The residue was dissolved in the minimum amount of methanol and passed through a silica gel column(2.54×15 cm) with aid of additional methanol. One hundred ml. of effluent was collected and concentrated. During the concentration, a precipitate was formed. The white precipitate was filtered and dried at room temperature in vacuo, yielding 2.04 g. (86.8%); m.p. 207°-209°(dec.). (Lit. m.p. 207°-210°(83), m.p. 211°-212°(32), m.p. 205°-207°(86). at 0° well closed The mixture was evaporated to a syrupy material below 30° in vacuo The residue was dissolved in the minimum amount of methanol of effluent was collected concentrated During the concentration a precipitate was formed The white precipitate was filtered dried at room temperature in vacuo yielding 2.04 g