N-(octadecanoyl)-sphinganine

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (5.00 g, 8.17 mmol) synthesized in the same manner as Example 17 was added to a THF suspension (48 mL) containing sodium borohydride (0.62 mg, 16.34 mmol) at 0° C. for 5 hour. After completion of the dropwise addition, calcium chloride (1.82 mg, 16.40 mmol) was added for 1 hour. After water was added to the reaction mixture, concentrated hydrochloric acid was added thereto to adjust pH of the mixture to be 1.5. The mixture was further stirred at 50° C. for 1 hour, and the organic layer was separated. It was confirmed by comparative analysis of the organic layer with sample product using HPLC that the organic layer contained 4.41 g of the title compound (yield: 95%). It was also found that anti-form:syn-form was 98:2 and the optical purity of the anti-form was 99% ee. was added for 1 hour was added the organic layer was separated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (1.50 g, 2.46 mmol) synthesized in the same manner as Example 17 was added to a THF suspension (15 mL) containing sodium borohydride (271.9 mg, 7.38 mmol) at room temperature for 0.5 hours. After completion of the dropwise addition, aluminum chloride (984.0 mg, 7.38 mmol) was added for 1 hour. After water was added to the reaction mixture, concentrated hydrochloric acid was added thereto to adjust pH of the mixture to be 1.5. The resulting reaction mixture was further stirred at 50° C. for 1 hour, and the organic layer was separated. It was confirmed by comparative analysis of the organic layer with sample product using HPLC that the organic layer contained 1.18 g of the title compound (yield: 84%). It was also found that anti-form:syn-form was 98:2 and the optical purity of the anti-form was 97% ee. was added for 1 hour was added The resulting reaction mixture the organic layer was separated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A THF suspension (2 mL) containing sodium borohydride (39.2 mg, 0.96 mmol) was heated to 60° C., and ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (300.0 mg, 0.49 mmol) synthesized in the same manner as Example 17 was added for 2.5 hours. After completion of the dropwise addition, the mixture was further stirred at 60° C. for 24 hours. After ethyl acetate and water were added thereto, the reaction mixture was stirred at 60° C. for 1 hour. After the organic layer was separated, the obtained organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was removed in reduced pressure. It was confirmed that 219.4 mg of the title compound was contained (yield: 78%). HPLC analysis was carried out to find that anti-form:syn-form was 81:19 and the optical purity of the anti-form was 99% ee. was added for 2.5 hours After completion of the dropwise addition the reaction mixture was stirred at 60° C. for 1 hour After the organic layer was separated the obtained organic layer was washed with saturated brine dried with magnesium sulfate The solvent was removed in reduced pressure

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A t-butyl methyl ether suspension (2 mL) containing ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (100 mg. 0.16 mmol) synthesized in the same method as Example 17 and sodium borohydride (20.3 mg, 0.54 mmol) was stirred at 23° C. for 48 hours. After water (5 mL) was added thereto, the reaction mixture was separated at 40° C. to separate the organic layer. It was confirmed by comparative analysis of the obtained organic layer with sample product using HPLC that the organic layer contained 86.6 mg of the title compound (yield: 93%). HPLC analysis was carried out to find that anti-form:syn-form was 93:7 and the optical purity of the anti-form was 100% ee. the reaction mixture was separated at 40° C. to separate the organic layer

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (5.00 g, 8.17 mmol) synthesized in the same manner as Example 17 was added to a THF suspension (48 mL) containing sodium borohydride (0.62 mg, 16.34 mmol) at 0° C. for 5 hour. After completion of the dropwise addition, calcium chloride (1.82 mg, 16.40 mmol) was added for 1 hour. After water was added to the reaction mixture, concentrated hydrochloric acid was added thereto to adjust pH of the mixture to be 1.5. The mixture was further stirred at 50° C. for 1 hour, and the organic layer was separated. It was confirmed by comparative analysis of the organic layer with sample product using HPLC that the organic layer contained 4.41 g of the title compound (yield: 95%). It was also found that anti-form:syn-form was 98:2 and the optical purity of the anti-form was 99% ee. was added for 1 hour was added the organic layer was separated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (1.50 g, 2.46 mmol) synthesized in the same manner as Example 17 was added to a THF suspension (15 mL) containing sodium borohydride (271.9 mg, 7.38 mmol) at room temperature for 0.5 hours. After completion of the dropwise addition, aluminum chloride (984.0 mg, 7.38 mmol) was added for 1 hour. After water was added to the reaction mixture, concentrated hydrochloric acid was added thereto to adjust pH of the mixture to be 1.5. The resulting reaction mixture was further stirred at 50° C. for 1 hour, and the organic layer was separated. It was confirmed by comparative analysis of the organic layer with sample product using HPLC that the organic layer contained 1.18 g of the title compound (yield: 84%). It was also found that anti-form:syn-form was 98:2 and the optical purity of the anti-form was 97% ee. was added for 1 hour was added The resulting reaction mixture the organic layer was separated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A THF suspension (2 mL) containing sodium borohydride (39.2 mg, 0.96 mmol) was heated to 60° C., and ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (300.0 mg, 0.49 mmol) synthesized in the same manner as Example 17 was added for 2.5 hours. After completion of the dropwise addition, the mixture was further stirred at 60° C. for 24 hours. After ethyl acetate and water were added thereto, the reaction mixture was stirred at 60° C. for 1 hour. After the organic layer was separated, the obtained organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was removed in reduced pressure. It was confirmed that 219.4 mg of the title compound was contained (yield: 78%). HPLC analysis was carried out to find that anti-form:syn-form was 81:19 and the optical purity of the anti-form was 99% ee. was added for 2.5 hours After completion of the dropwise addition the reaction mixture was stirred at 60° C. for 1 hour After the organic layer was separated the obtained organic layer was washed with saturated brine dried with magnesium sulfate The solvent was removed in reduced pressure

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A t-butyl methyl ether suspension (2 mL) containing ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (100 mg. 0.16 mmol) synthesized in the same method as Example 17 and sodium borohydride (20.3 mg, 0.54 mmol) was stirred at 23° C. for 48 hours. After water (5 mL) was added thereto, the reaction mixture was separated at 40° C. to separate the organic layer. It was confirmed by comparative analysis of the obtained organic layer with sample product using HPLC that the organic layer contained 86.6 mg of the title compound (yield: 93%). HPLC analysis was carried out to find that anti-form:syn-form was 93:7 and the optical purity of the anti-form was 100% ee. the reaction mixture was separated at 40° C. to separate the organic layer

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (5.00 g, 8.17 mmol) synthesized in the same manner as Example 17 was added to a THF suspension (48 mL) containing sodium borohydride (0.62 mg, 16.34 mmol) at 0° C. for 5 hour. After completion of the dropwise addition, calcium chloride (1.82 mg, 16.40 mmol) was added for 1 hour. After water was added to the reaction mixture, concentrated hydrochloric acid was added thereto to adjust pH of the mixture to be 1.5. The mixture was further stirred at 50° C. for 1 hour, and the organic layer was separated. It was confirmed by comparative analysis of the organic layer with sample product using HPLC that the organic layer contained 4.41 g of the title compound (yield: 95%). It was also found that anti-form:syn-form was 98:2 and the optical purity of the anti-form was 99% ee. was added for 1 hour was added the organic layer was separated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (1.50 g, 2.46 mmol) synthesized in the same manner as Example 17 was added to a THF suspension (15 mL) containing sodium borohydride (271.9 mg, 7.38 mmol) at room temperature for 0.5 hours. After completion of the dropwise addition, aluminum chloride (984.0 mg, 7.38 mmol) was added for 1 hour. After water was added to the reaction mixture, concentrated hydrochloric acid was added thereto to adjust pH of the mixture to be 1.5. The resulting reaction mixture was further stirred at 50° C. for 1 hour, and the organic layer was separated. It was confirmed by comparative analysis of the organic layer with sample product using HPLC that the organic layer contained 1.18 g of the title compound (yield: 84%). It was also found that anti-form:syn-form was 98:2 and the optical purity of the anti-form was 97% ee. was added for 1 hour was added The resulting reaction mixture the organic layer was separated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A THF suspension (2 mL) containing sodium borohydride (39.2 mg, 0.96 mmol) was heated to 60° C., and ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (300.0 mg, 0.49 mmol) synthesized in the same manner as Example 17 was added for 2.5 hours. After completion of the dropwise addition, the mixture was further stirred at 60° C. for 24 hours. After ethyl acetate and water were added thereto, the reaction mixture was stirred at 60° C. for 1 hour. After the organic layer was separated, the obtained organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was removed in reduced pressure. It was confirmed that 219.4 mg of the title compound was contained (yield: 78%). HPLC analysis was carried out to find that anti-form:syn-form was 81:19 and the optical purity of the anti-form was 99% ee. was added for 2.5 hours After completion of the dropwise addition the reaction mixture was stirred at 60° C. for 1 hour After the organic layer was separated the obtained organic layer was washed with saturated brine dried with magnesium sulfate The solvent was removed in reduced pressure

Conditions: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A t-butyl methyl ether suspension (2 mL) containing ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (100 mg. 0.16 mmol) synthesized in the same method as Example 17 and sodium borohydride (20.3 mg, 0.54 mmol) was stirred at 23° C. for 48 hours. After water (5 mL) was added thereto, the reaction mixture was separated at 40° C. to separate the organic layer. It was confirmed by comparative analysis of the obtained organic layer with sample product using HPLC that the organic layer contained 86.6 mg of the title compound (yield: 93%). HPLC analysis was carried out to find that anti-form:syn-form was 93:7 and the optical purity of the anti-form was 100% ee. the reaction mixture was separated at 40° C. to separate the organic layer