Methanol → 2-[3-(2-Chloroethyl)-3-nitrosoureido]-D-glucopyranose

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Reaction Steps

1.79 g (10 mmol) of 2-amino-2-deoxy-D-glucopyranose is dissolved in a mixture of 10 ml methanol and 5 ml dimethyl sulfoxide, and this solution is 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 methylene chloride and 10 ml tetrahydrofuran, while stirring, at 20°-25° C. over 10 minutes. The resultant mixture is stirred at the same temperature for a further 1.5 hours. The thus reacted solution is concentrated at 40° C. and below, under reduced pressure. The crystalline residue obtained is washed with petroleum ether, dried under reduced pressure, and recrystallized from ethanol to give 2.56 g of 3-(D-glucopyranos-2-yl)-1-(2-chloroethyl)-1-nitrosourea. Yield 81.6%. mp 147°-148° C. (decomp.). Analysis for C9H16N3O7Cl (MW 313.69):

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