Formic Acid → N-(2-Chloroethyl)-N'-beta-D-glucopyranosyl-N-nitrosourea

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Reaction Steps

1.79 g (10 mmol) of 1-amino-1-deoxy-β-D-glucopyranose is dissolved in a mixture of 20 ml methanol and 10 ml dioxane, and to this solution is added a mixture of formic acid and citric acid dropwise, with stirring, to adjust the PH of the solution to 9.1. The resulting solution is then added dropwise to a solution prepared by dissolving 3.28 g (12 mmol) of o-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate in a mixture of 10 ml tetrahydrofuran and 15 ml dioxane, while stirring, at 5°-10° C. over 30 minutes. The resultant mixture is stirred at the same temperature for a further 4 hours, and the thus reacted solution is concentrated at 40° C. and below, under reduced pressure. The crystalline residue obtained is washed with anhydrous ethyl ether and then with acetone, dried under reduced pressure, and recrystallized from anhydrous ethanol-ethyl ether (4:1) to give 2.56 g of 3-(β-D-glucopyranosyl)-1-(2-chloroethyl)-1-nitrosourea. Yield 81.5%. mp 77°-78° C. (decomp.). [α]D25 -10.3° (C 1.0, water). Analysis for C9H16N3O7Cl (MW 313.69):

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