1-Butanol → 2,6-Anhydro-1-deoxy-1-nitro-D-glycero-D-gulo-heptitol

50 g of moisture-free D-glucose are dissolved in 200 ml dimethyl sulphoxide and 100 ml methanol. 100 ml nitromethane and a suspension of 30 g sodium methylate in 320 ml methanol are added to the latter and stirring takes place for 24 hours at room temperature. 250 ml n-butanol are added to the reaction mixture and stirred for 1 hour at 0° C. The latter is then filtered and the residue washed with 100 ml isopropanol and 100 ml diethyl ether. After drying, 71 g of a bright yellow powder are obtained. The latter is dissolved in 200 ml water and passed through a column with 100 g of cation exchanger (Aldrich, Amberlyst 15, strongly acid H+ form). The ion exchanger is washed with 500 ml water. The aqueous, red solution is concentrated to 100 ml and heated to 90 ° C. over 30 hours. 2 g of fine activated carbon are added to the hot solution, which is then stirred for 10 minutes, filtered through 5 g kieselguhr and rewashed with 200 ml water.

1. additionare added to the latter
2. customfor 24 hours
3. customat room temperature
4. stirringstirred for 1 hour at 0° C
5. filtrationThe latter is then filtered
6. washthe residue washed with 100 ml isopropanol and 100 ml diethyl ether
7. customAfter drying

ORD record

ord-a085632de1cb4763bcf32bc5dd1f2f56

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05556836