Carbon Dioxide → 3-(D-glucopyranos-6-yl)-1-(2-chloroethyl)-1-nitrosourea

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Reaction Steps

1.79 g (10 mmol) of 6-amino-6-deoxy-D-glucopyranose is dissolved in a mixture of 20 ml anhydrous ethanol and 20 ml dimethyl sulfoxide, and the solution is cooled to 0°-5° C. To this solution is added 3.3 g (75 mmol) of dry-ice little by little so as to convert the glucopyranose into its carbonic acid-addition salt. This acid-addition salt 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 40 ml anhydrous tetrahydrofuran and 10 ml toluene, while stirring, at 0°-5° C. over 30 minutes. The resultant mixture is stirred further at 20°-25° C. for 2 hours, and the thus reacted solution is concentrated at 40° C. and below, under reduced pressure. To the oily residue thus produced is added 80 ml of ethyl ether and the solution is left at 4° C. overnight. The crystalline residue obtained is washed with chloroform and then with ethyl ether, dried under reduced pressure, and recrystallized from anhydrous ethanol-n-hexane (4:1) to give 2.70 g of 3-(D-glucopyranos-6-yl)-1-(2-chloroethyl)-1-nitrosourea. Yield 86.1%. mp 102°-103° C. (decomp.). [α]D20 +55° (C 0.5, methanol; the value of +55° reduced to +37° after 18 hours). Analysis for C9H16N3O7Cl (MW 313.69):

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