(2R,3R,4R,5S)-6-(butylamino)hexane-1,2,3,4,5-pentol

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction solution is prepared by adding 81 gm N-n-butylglucamine hydrochloride to 640 ml of water in a 1-L bioreactor. The solution, which is pH 5, is cooled to about 15° C. A total of 70 gin (wet weight) of washed G. oxydans cell paste is added and the reaction mixture is agitated (400 rmp) and aerated (0.5 vvm) while controlling the temperature at 15° C. and pH at 5. After 20 hours, the HPLC assay indicates that over 99% of the N-n-butylglucamine has been converted for a 80% yield of 6-n-butylamino-6-deoxy-α-L-sorbofuranose. A reaction solution is prepared oxydans cell paste is added at 15° C.

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction solution is prepared by adding 46 gm N-n-butylglucamine to 620 ml of water in a 1-L bioreactor. The suspension is adjusted to pH 5 (with concentrated hydrochloric acid) and cooled to about 15° C. A total of 30 gm (wet weight) of washed G. oxydans cell paste is added and the reaction mixture is agitated (350 rpm) and aerated (0.2 vvm) while controlling the temperature at 15° C. and pH at 5. After 77 hours, the HPLC assay indicates that over 97% of the substrate has been converted for a 75% yield of 6-n-butylamino-6-deoxy-α-L-sorbofuranose. A reaction solution is prepared oxydans cell paste is added at 15° C.

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction solution is prepared by adding 46 gm N-n-butylglucamine to 620 ml of water in a 1-L bioreactor. The suspension is adjusted to pH 5 (with concentrated hydrochloric acid) and cooled to about 15° C. A total of 30 gm (wet weight) of washed G. oxydans cell paste is added and the reaction mixture is agitated (350 rpm) and aerated (0.2 vvm) while controlling the temperature at 15° C. and pH at 5. After 77 hours, the HPLC assay indicates that over 97% of the substrate has been converted for a 75% yield of 6-n-butylamino-6-deoxy-α-L-sorbofuranose. A reaction solution is prepared oxydans cell paste is added at 15° C.

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction solution is prepared by adding 750 gm N-n-butylglucamine to 7.2 L of water in a 10-L bioreactor. The suspension is adjusted to pH 5 (with concentrated HCl ) and cooled to about 15° C. A total of 300 gm (wet weight) of washed G. oxydans cell paste is added and the reaction mixture is agitated (350-500 rpm) and aerated (0.4 vvm) while controlling the temperature at 15° C. and pH at 5. After 14 hours, the HPLC assay indicates that over 97% of the substrate has converted for a 85% yield of 6-n-butylamino-6-deoxy-α-L-sorbofuranose. A reaction solution is prepared oxydans cell paste is added at 15° C.

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction solution is prepared by adding 91 gm N-n-butylglucamine to 580 ml of water in a 1-L bioreactor. The suspension is adjusted to about pH 5 (with concentrated HCl ) and cooled to about 15° C. A total of 24 gm (wet weight) of washed G. oxydans cell paste is added and the reaction mixture is agitated (500 rpm) and aerated (0.5 vvm) while controlling the temperature at 15° C. and pH at 5. After 23 hours, the HPLC assay indicates that over 99% of the substrate has converted for a 83% yield of 6-n-butylamino-6-deoxy-α-L-sorbofuranose. A reaction solution is prepared oxydans cell paste is added at 15° C.

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction solution is prepared by adding 91 gm N-n-butylglucamine to 580 ml of water in a 1-L bioreactor. The suspension is adjusted to about pH 5 (with concentrated HCl ) and cooled to about 15° C. A total of 24 gm (wet weight) of washed G. oxydans cell paste is added and the reaction mixture is agitated (500 rpm) and aerated (0.5 vvm) while controlling the temperature at 15° C. and pH at 5. After 23 hours, the HPLC assay indicates that over 99% of the substrate has converted for a 83% yield of 6-n-butylamino-6-deoxy-α-L-sorbofuranose. A reaction solution is prepared oxydans cell paste is added at 15° C.

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

Procedure: A 2.3 L Parr shaker bottle is charged with 1 L of 3A ethanol and 83 g (1.1 mol) of n-butylamine. The mixture is stirred and cooled while 16 mL of 12N hydrochloric acid is slowly added. The pH after this addition is 10. To the 2.3 L Parr bottle is added 200 g (1.1 mol) of D-glucose followed by 60 g of 4% palladium-on-carbon (50% water-wet). The mixture is agitated rapidly and hydrogenated at a constant pressure of 4 arm of hydrogen at 60°±5° C. until the reaction is complete (as indicated by hydrogen uptake). The hydrogen is vented and the 4% palladium-on-carbon is removed by filtration through a layer of powdered cellulose. The catalyst is washed with 100 ml, of 3A ethanol followed by 50 mL of water. The wash is combined with the filtrate to give a solution containing a mixture of N-butyl glucamine and the corresponding hydrochloride salt. The mixture is stirred and cooled while 80 mL of 12N hydrochloric add is slowly added. The pH after this addition is 2.5. The ethanol is removed by distillation under reduced pressure. The residue contains approximately 270 g of N-n-butyl glucamine hydrochloride. The residue is diluted to 500 mL with water to produce a bulk solution of N-n-butyl glucamine hydrochloride which is used in the next step without purification. is slowly added The pH after this addition The mixture is agitated rapidly the 4% palladium-on-carbon is removed by filtration through a layer of powdered cellulose The catalyst is washed with 100 ml, of 3A ethanol to give a solution containing The mixture is stirred cooled while 80 mL of 12N hydrochloric add is slowly added The pH after this addition The ethanol is removed by distillation under reduced pressure The residue is diluted to 500 mL with water

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

Procedure: A 2.3 L Parr shaker bottle is charged with 1 L of 3A ethanol and 83 g (1.1 mol) of n-butylamine. The mixture is stirred and cooled while 16 mL of 12N hydrochloric acid is slowly added. The pH after this addition is 10. To the 2.3 L Parr bottle is added 200 g (1.1 mol) of D-glucose followed by 60 g of 4% palladium-on-carbon (50% water-wet). The mixture is agitated rapidly and hydrogenated at a constant pressure of 4 arm of hydrogen at 60°±5° C. until the reaction is complete (as indicated by hydrogen uptake). The hydrogen is vented and the 4% palladium-on-carbon is removed by filtration through a layer of powdered cellulose. The catalyst is washed with 100 ml, of 3A ethanol followed by 50 mL of water. The wash is combined with the filtrate to give a solution containing a mixture of N-butyl glucamine and the corresponding hydrochloride salt. The mixture is stirred and cooled while 80 mL of 12N hydrochloric add is slowly added. The pH after this addition is 2.5. The ethanol is removed by distillation under reduced pressure. The residue contains approximately 270 g of N-n-butyl glucamine hydrochloride. The residue is diluted to 500 mL with water to produce a bulk solution of N-n-butyl glucamine hydrochloride which is used in the next step without purification. is slowly added The pH after this addition The mixture is agitated rapidly the 4% palladium-on-carbon is removed by filtration through a layer of powdered cellulose The catalyst is washed with 100 ml, of 3A ethanol to give a solution containing The mixture is stirred cooled while 80 mL of 12N hydrochloric add is slowly added The pH after this addition The ethanol is removed by distillation under reduced pressure The residue is diluted to 500 mL with water

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

Procedure: The process of claim 1 in which D-glucose is aminated to N-n-butyl glucamine which in turn is oxidized to produce 6-n-butylamino-6-deoxy-α-L-sorbofuranose which is reduced to produce N-n-butyl-1-deoxynojirimycin.

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction solution is prepared by adding 81 gm N-n-butylglucamine hydrochloride to 640 ml of water in a 1-L bioreactor. The solution, which is pH 5, is cooled to about 15° C. A total of 70 gm (wet weight) of washed G. oxydans cell paste is added and the reaction mixture is agitated (400 rmp) and aerated (0.5 vvm) while controlling the temperature at 15° C. and pH at 5. After 20 hours, the HPLC assay indicates that over 99% of the N-n-butylglucamine has been converted for a 80% yield of 6-n-butylamino-6-deoxy-α-L-sorbofuranose. A reaction solution is prepared oxydans cell paste is added at 15° C.

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction solution is prepared by adding 46 gm N-n-butylglucamine to 620 ml of water in a 1-L bioreactor. The suspension is adjusted to pH 5 (with concentrated hydrochloric acid) and cooled to about 15° C. A total of 30 gm (wet weight) of washed G. oxydans cell paste is added and the reaction mixture is agitated (350 rpm) and aerated (0.2 vvm) while controlling the temperature at 15° C. and pH at 5. After 77 hours, the HPLC assay indicates that over 97% of the substrate has been converted for a 75% yield of 6-n-butylamino-6-deoxy-α-L-sorbofuranose. A reaction solution is prepared oxydans cell paste is added at 15° C.

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A reaction solution is prepared by adding 750 gm N-n-butylglucamine to 7.2 L of water in a 10-L bioreactor. The suspension is adjusted to pH 5 (with concentrated HCl) and cooled to about 15° C. A total of 300 gm (wet weight) of washed G. oxydans cell paste is added and the reaction mixture is agitated (350-500 rpm) and aerated (0.4 vvm) while controlling the temperature at 15° C. and pH at 5. After 14 hours, the HPLC assay indicates that over 97% of the substrate has converted for a 85% yield of 6-n-butylamino-6-deoxy-α-L-sorbofuranose. A reaction solution is prepared oxydans cell paste is added at 15° C.