856765-86-1

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 117168-59-9 (2S,3S,4R)-2-azido-1,3,4-octadecanetriol 
• 554-62-1 D-ribo-phytosphingosine 
• 856765-85-0 (4R,5R)-4-((E)-Pentadec-1-enyl)-2-phenyl-[1,3]dioxan-5-ol 
• 121998-84-3 (2R,3R,4E)-octadec-4-ene-1,2,3-triol 

Downstream Products

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 103348-49-8 2-azido-sphingosine 

Relevant academic research and scientific papers

A rapid synthesis of sphingosine from phytosphingosine

A simple and efficient protocol for the synthesis of a sphingosine starting from cost-effective phytosphingosine has been described. Two alternative synthetic pathway have been disclosed based on the use of two different kinds of protective groups for the protection of the amino group in the phytosphingosine. The protected phytosphingosine was subsequently transformed into sphingosine in 5 steps i.e. protection of the amine group, protection of 1,3-diol, leaving group insertion, elimination, and one-pot deprotection.

D-erythro-sphingosine synthesis method

The invention relates to a D-erythro-sphingosine synthesis method, comprising the steps of dissolving a compound 6 into dry tetrahydrofuran, adding lithium aluminum hydride under protection of nitrogen, after complete reaction of a raw material, adding a potassium sodium tartrate solution and finishing; extracting through ethyl acetate, concentrating and performing column chromatography; separating to obtain D-erythro-sphingosine. Compared with a traditional method, the synthesis method provided by the invention has the advantages that the use of a large amount of strong base phenyl lithium in a Wittig reaction process is avoided, meanwhile, the yield is increased; an azidation reaction adopts a two-step method of iodination and then azidation, and low temperature reaction in the existing technical scheme is not needed, so that the operation is more convenient and simple.

Stereoselective Synthesis of D(+)-erythro and L(-)-threo Sphingosines from Carbohydrates

Stereocontrolled syntheses of D(+)-erythro and L(-)-threo shingosines are described starting from D-xylose and D-arabinose respectively through acetylenic intermediates 3 and 4, obtained by base induced double elimination of the β-alkoxy chlorides 5 and 13. Keywords: D(+)-erythro and L(-)-threo sphingosines; base induced double elimination reaction; acetylenic alcohol