- Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine
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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.
- Van Den Berg, Richard J. B. H. N.,Korevaar, Cornelius G. N.,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Van Boom, Jacques H.
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p. 5699 - 5704
(2007/10/03)
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- A process for the synthesis of sphingosine
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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 NH2 group with a NH2 protecting group,(3) activating C4 HR3' for an elimination reaction with C5HR4,(4) causing an elimination reaction to take place to form a double bond between the C4 and C5 carbon atom,(5) removing the NH2 protecting group.
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- Process for the synthesis of sphingosine
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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
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- The synthesis and biological characterization of a ceramide library
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A facile synthesis of a combinatorial ceramide library and their activities in the NF-κB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-κB activating molecule was discovered among ceramide containing β-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated. Copyright
- Chang, Young-Tae,Choi, Jaehwa,Ding, Sheng,Prieschl, Eva E.,Baumruker, Thomas,Lee, Jae-Mok,Chung, Sung-Kee,Schultz, Peter G.
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p. 1856 - 1857
(2007/10/03)
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