Synthesis of threo-4,5-dihydroxy diastereomers of sphinganine;.
The threo-4,5-dihydroxy diastereomers of sphinganine were prepared by the following sequence of reactions: (a) benzoylation of sphingenine to the tribenzoyl derivative; (b) osmylation followed by resolution of the mixture of threo-4,5-dihydroxy tribenzoyl (DHTBS) diastereomers; and (c) alkaline hydrolysis to yield the threo-4,5-dihydroxysphinganines (DHS). Carbon atoms 4 and 5 of the high and low melting threo-4,5-DHTBS diastereomers and the compounds derived from them were tentatively assigned 4R, 5S and 5R configurations, respectively;
D000605:Amino Alcohols / Q000138:chemical synthesis*; D000818:Animals; D001593:Benzyl Compounds; D001923:Brain Chemistry; D002417:Cattle; D002845:Chromatography; D008722:Methods; D008968:Molecular Conformation; D012822:Silicon Dioxide; D013055:Spectrophotometry, Infrared; D013107:Sphingolipids; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013237:Stereoisomerism
D000605:Amino Alcohols; D001593:Benzyl Compounds; D013107:Sphingolipids; D012822:Silicon Dioxide; D013110:Sphingosine