Synthesis of (R)-[2-2H]isopentenyl diphosphate and determination of its enantiopurity by 2H NMR spectroscopy in a lyotropic medium.
[formula: see text] The synthesis of (R)-[2-2H]isopentenyl diphosphate from D-mannitol 1,2:5,6-bis-acetonide in 10 steps is reported. Stereospecific incorporation of the label is achieved by a BF3-catalyzed NaCNBD3 reduction of the enantiomerically pure (S)-isopropylidene oxirane intermediate. The enantiomeric excess of the penultimate precursor [2-2H]isopentenyl tosylate (> 95% ee) was determined by 2H NMR spectroscopy in a poly-gamma-benzyl-L-glutamate/CH2Cl2 liquid crystal at -50 degrees C.
Leyes
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Department of Chemistry, University of Utah, Salt Lake City 84112, USA.
Poulter
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D045782:Hemiterpenes; D006859:Hydrogen; D009682:Magnetic Resonance Spectroscopy; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism
D045782:Hemiterpenes; D009943:Organophosphorus Compounds; C004809:isopentenyl pyrophosphate; D006859:Hydrogen