1987-40-2Relevant articles and documents
Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine
Van Den Berg, Richard J. B. H. N.,Korevaar, Cornelius G. N.,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Van Boom, Jacques H.
, p. 5699 - 5704 (2007/10/03)
The synthesis of naturally occurring D-erythro-(2R,3S,4E)-sphingosine from commercially available D-ribo-(2S,3S,4R)-phytosphingosine is described. The key step in the reaction sequence comprises TMSI/DBN promoted regio- and stereoselective oxirane opening of intermediate 2-phenyl-4-(S)-[(1S,2S)-1,2- epoxyhexadecyl]-1,3-oxazoline followed by the in situ trans-elimination of 2-phenyl-4-(S)-[(1S,2R)-1,2-dideoxy-2-iodo-1-trimethylsilyloxyhexadecyl]-1, 3-oxazoline.
Process for the synthesis of sphingosine
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, (2008/06/13)
This invention relates to a method for the production of a sphingoid base according to formula comprising the steps of (1) dissolving a starting compound according to formula III or a salt thereof in a substantially inert solvent, (2) protecting the NHsu