Synthesis of D-erythro-sphingomyelin and of D-erythro-ceramide-1-phosphoinositol
โ Scribed by Bernd Kratzer; Thomas G. Mayer; Richard R. Schmidt
- Publisher
- Elsevier Science
- Year
- 1993
- Tongue
- French
- Weight
- 244 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0040-4039
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๐ SIMILAR VOLUMES
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
The readily available 2,3:4,5-di-O-cyclohexylidene-D-myo-with the D-erythro-azidophytosphingosine-derived ceramide-1-phosphite derivative 17 led, after oxidation and re-inositol derivative 3 was converted into the 1-O-unprotected D-myo-inositol derivative 6. Reaction with the phosphite moval of the
In their synthesis of dihydrosphingosine, Rozrsh and Adum [ 131 observed the formation of a I :1 mixture of two isomeric oxazolidinones resulting from an intramolecular transacylation: under our conditions, however, only 9 was obtained. We thank Prof. Dr. W . Roush for a preliminary communication of
D-erythro-sphingosine and D-esythro-sphinganine can be produced in protected form from serine by a synthetic approach in which the normal biological intermediate 3-ketosphinganine in protectyed form, is a key synthetic intermediate. The sequence is short and convergent, proceeds in good overall yiel