(3R,4S,5R,6R)-6-(hydroxymethyl)piperidine-2,3,4,5-tetrol

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

Procedure: A 300 g amount of nojirimycin was dissolved in 1.5 l of distilled water to which was added 80 g of deoxin-1, i.e., a crude powder of glucose oxidase with 10,000 units per mg which is produced by Penicillium amagasakiensis (produced by Nagase Sangyo Co./Japan). The pH of the reaction mixture was adjusted to 6.0 and then the reaction was conducted at 30°C in a 30 l jar fermenter with agitation at 300 r.p.m. under air-flowing conditions. After 65 hours of reaction, the reaction solution was passed through a column filled with Amberlite IR-120 (H+ type, 1.5 l). The column was then washed with 7 l of water. The treated solution and the washings were combined (22 l), and the combined solution was then neutralized with Amberlite IR-45 (OH- type), followed by decolorization with 50 g of carbon powder. The decolorized solution was then condensed. To the condensed solution (500 ml) was added 100 ml of methanol, which was allowed to stand to cool in order to yield a crystalline product. The crystals were separated from the solution by filtration to give 220 g of D-gluconic-δ-lactam as needle-like white crystals (yield of 77%). was added 80 g of deoxin-1, i.e.

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

Procedure: A 300 g amount of nojirimycin was dissolved in 1.5 l of distilled water to which was added 80 g of deoxin-1, i.e., a crude powder of glucose oxidase with 10,000 units per mg which is produced by Penicillium amagasakiensis (produced by Nagase Sangyo Co./Japan). The pH of the reaction mixture was adjusted to 6.0 and then the reaction was conducted at 30°C in a 30 l jar fermenter with agitation at 300 r.p.m. under air-flowing conditions. After 65 hours of reaction, the reaction solution was passed through a column filled with Amberlite IR-120 (H+ type, 1.5 l). The column was then washed with 7 l of water. The treated solution and the washings were combined (22 l), and the combined solution was then neutralized with Amberlite IR-45 (OH- type), followed by decolorization with 50 g of carbon powder. The decolorized solution was then condensed. To the condensed solution (500 ml) was added 100 ml of methanol, which was allowed to stand to cool in order to yield a crystalline product. The crystals were separated from the solution by filtration to give 220 g of D-gluconic-δ-lactam as needle-like white crystals (yield of 77%). was added 80 g of deoxin-1, i.e.

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

Procedure: 179 mg of nojirimycin is dissolved in 20 ml of water, followed by adding 1 ml of formalin, adding 100 mg of platinum on carbon catalyst and carrying out a catalytic reduction at ordinary temperature and under atmospheric pressure. The following treatments are carried out in the same manner as in Example 2 to obtain 150 mg (85%) of N-methyl moranoline.

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

Procedure: 179 mg of nojirimycin is dissolved in 20 ml of a 50% water-containing ethanol, followed by adding 1 ml of formalin, adding 100 mg of palladium on carbon catalyst and carrying out a catalytic reduction at ordinary temperature and under atmospheric pressure. The subsequent treatments are carried out in the same manner as in Example 2 to obtain 144 mg (81%) of N-methyl moranoline.

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

Procedure: 179 mg of nojirimycin is dissolved in 20 ml of water, followed by adding 1 ml of formalin, adding about 0.5 ml of Raney nickel catalyst and stirring in a hydrogen stream, at ordinary temperature, under atmospheric pressure, for 3 hours. After completion of the reaction, the catalyst is separated by filtration; the resulting filtrate is passed through a column containing about 100 ml of Dowex 50 W×4 (H); and after washing the column, the resulting adsorbed substances are eluted with 1% aqueous ammonia. The resulting elute is brought to dryness under reduced pressure, and the remaining colorless crystal is recrystallized from ethanol to obtain N-methyl moranoline. After completion of the reaction the catalyst is separated by filtration containing about 100 ml of Dowex 50 W×4 (H) and after washing the column the resulting adsorbed substances are eluted with 1% aqueous ammonia The resulting elute the remaining colorless crystal is recrystallized from ethanol

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

Procedure: A 300 g amount of nojirimycin was dissolved in 1.5 l of distilled water to which was added 80 g of deoxin-1, i.e., a crude powder of glucose oxidase with 10,000 units per mg which is produced by Penicillium amagasakiensis (produced by Nagase Sangyo Co./Japan). The pH of the reaction mixture was adjusted to 6.0 and then the reaction was conducted at 30°C in a 30 l jar fermenter with agitation at 300 r.p.m. under air-flowing conditions. After 65 hours of reaction, the reaction solution was passed through a column filled with Amberlite IR-120 (H+ type, 1.5 l). The column was then washed with 7 l of water. The treated solution and the washings were combined (22 l), and the combined solution was then neutralized with Amberlite IR-45 (OH- type), followed by decolorization with 50 g of carbon powder. The decolorized solution was then condensed. To the condensed solution (500 ml) was added 100 ml of methanol, which was allowed to stand to cool in order to yield a crystalline product. The crystals were separated from the solution by filtration to give 220 g of D-gluconic-δ-lactam as needle-like white crystals (yield of 77%). was added 80 g of deoxin-1, i.e.