N-Boc sphingosine

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The tert-butyl (2S,3R)-1,3-dihydroxyoctadec-4-yn-2-ylcarbamate (85 mg, 0.21 mmol) obtained in the above-described reaction was dissolved in THF (21 ml) and cooled to 0° C.; a 65% toluene solution of sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al) (258 μl, 0.850 mmol) was subsequently added dropwise. The resulting mixture was heated to room temperature and stirred for 2.5 hours. 1 M hydrochloric acid was subsequently added to the mixture, and the reaction was stopped; the mixture was extracted with diethylether, and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography to produce N-tert-butoxycarbonyl sphingosine (52 mg, 64%). The resulting mixture was heated to room temperature the mixture was extracted with diethylether the organic layer was dried over anhydrous sodium sulfate filtered concentrated The concentrate was purified by silica gel column chromatography

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The tert-butyl (2S,3R)-1,3-dihydroxyoctadec-4-yn-2-ylcarbamate (85 mg, 0.21 mmol) obtained in the above-described reaction was dissolved in THF (21 ml) and cooled to 0° C.; a 65% toluene solution of sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al) (258 μl, 0.850 mmol) was subsequently added dropwise. The resulting mixture was heated to room temperature and stirred for 2.5 hours. 1 M hydrochloric acid was subsequently added to the mixture, and the reaction was stopped; the mixture was extracted with diethylether, and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography to produce N-tert-butoxycarbonyl sphingosine (52 mg, 64%). The resulting mixture was heated to room temperature the mixture was extracted with diethylether the organic layer was dried over anhydrous sodium sulfate filtered concentrated The concentrate was purified by silica gel column chromatography

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The tert-butyl (2S,3R)-1,3-dihydroxyoctadec-4-yn-2-ylcarbamate (85 mg, 0.21 mmol) obtained in the above-described reaction was dissolved in THF (21 ml) and cooled to 0° C.; a 65% toluene solution of sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al) (258 μl, 0.850 mmol) was subsequently added dropwise. The resulting mixture was heated to room temperature and stirred for 2.5 hours. 1 M hydrochloric acid was subsequently added to the mixture, and the reaction was stopped; the mixture was extracted with diethylether, and the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography to produce N-tert-butoxycarbonyl sphingosine (52 mg, 64%). The resulting mixture was heated to room temperature the mixture was extracted with diethylether the organic layer was dried over anhydrous sodium sulfate filtered concentrated The concentrate was purified by silica gel column chromatography