Synthesis of D,L-erythro-sphingomyelins
โ Scribed by H. Alpes
- Publisher
- Elsevier Science
- Year
- 1974
- Tongue
- English
- Weight
- 348 KB
- Volume
- 13
- Category
- Article
- ISSN
- 0009-3084
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โฆ Synopsis
This paper describes an improved procedure for the reaction of the primary hydroxyl group of 3-O-benzoylceramides with 13-bromoethylphosphoryldichloride and for the subsequent reaction with trimethylamine (fig. 1). Column chromatography of the resulting reaction mixtures gives sphingomyelins and the corresponding ceramides in high purity. The procedure is generally applicable for the synthesis of sphingomyelins with saturated, unsaturated, and 2-hydroxy fatty acid chains.
๐ SIMILAR VOLUMES
## Isolated vield. \*) The free amine bases 1 4 are prone to air-oxidation and are difficult to handle.
2,4-Di-O-protected Pthreose, readily avaiZabZe from D-galactose, is a versatile intermediate for D-erythro-sphingosine syntheses via trans-selective Wittig reaction, azide introduction at the unprotected hydroxyZic group, and subsequent azide reduction.